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Top 5 Lifestyle Investing Considerations

Portrait Andrew Schulhof

#303-1338 West Broadway
British Columbia
V6H 1H2

Plane wing as it flies over Mexico
Lifestyle real estate investing means investing in real estate around the world that has a personal use case for yourself. There are several things to consider when considering whether or not you want to experience lifestyle investing, from the destination and weather to financial performance and cashflow.

Before I get into the TOP Five Lifestyle Investing Considerations, it is worth explaining what it is. My interpretation of ‘Lifestyle Investing’ as it relates to real estate is very different from what we consider “regular” real estate investing but also has similar elements. It involves investing in real estate in a destination location with a personal use component where the investor visits regularly or even lives there part of the year.  It may or may not be rented out for the remaining time. In my opinion, owning timeshares does not really fall under my interpretation of Lifestyle Investing because you own a block of time, not the real estate. Owning the real estate is a key defining component of Lifestyle Investing. One of the best ways to get started is asking as many questions of yourself and those that are already invested in the region you are interested.

Here are the TOP FIVE Lifestyle Investing Considerations

1. Global Destinations

For us in Canada, it typically involves sunny and warm regions to escape to during the cold periods of the year.

Lifestyle Investment destinations can be almost anywhere in the world, from locations in the Mediterranean, such as Portugal or Spain, to the multiple destinations in the Caribbean, which can include, Florida in the USA, various cities in Mexico and many Central American countries. Regions on the Pacific coast are also key destinations for Lifestyle Investing, which include many places in Canada, the USA, Mexico, and Central America. We can even go further afar such as Southeast Asia, places like the Philippines, Bali, Thailand, etc.

Those sun destinations don’t always involve oceans as many lifestyle investors like dryer climates such as Phoenix, Palm Springs, and Palm Desert, or regions in Utah.

It is not just limited to the colder months as Lifestyle Investments could include summer use properties right here in Canada such as cottage country in Ontario, the Okanagan, Gulf Islands, Vancouver Island in BC, Oceanfront cottages in Prince Edward Island and so many more.

Not only can Lifestyle Investing include the sun destinations, it can also include winter oriented resort type destinations such as Whistler, Banff, Mont Tremblant, Vail, Tahoe to name just a few.

As you may already know, we own in Maui which was our first lifestyle investment. I personally know of many lifestyle investors that have taken advantage of the above locations. Some rent their places out, and others don’t, depending on their personal wants and needs.

As you can see by listing the many examples, you need to choose the destination based on your desires and lifestyle.

2. Property Security

One of the absolute most important considerations is keeping your property secure. This not only includes the obvious of how safe do you feel, but also how safe is the ownership.


With recent weather-related natural disasters it is imperative that we think ahead and consider how climate change and weather patterns could impact the property. Can you get insurance and if so, from whom, how, and how much does it cost? What are the weather patterns or seasons in this location? This is important to understand for your stay and for your potential rental guests.

Safety & Crime

We must understand the real safety impact of the real estate market, specific area and property in which we are investing, beyond the headlines that we read. Ask people who already own there. We are never going to eliminate all dangers anywhere and target destinations are no different. It always comes down to doing your due diligence and being wise in how you conduct yourselves in any community. For instance, in many desirable destinations many Lifestyle investors will own a condo or some form of home in a gated community, which includes the security aspect, for peace of mind.

Form of Ownership

Some key considerations you need to know are: what does the purchase process look like, who is involved, and what is the form of tenure? A key component of owning a lifestyle investment property in your home country or another country is what form of ownership is available and what would work best for your particular situation. I strongly recommend discussing the potential liabilities with your professional legal counsel before you take action. Also discuss the tax implication of owing such a property and under what structure before you commit on paper. In many foreign countries there are ownership structures that work well there but not necessarily in Canada. Also, in many countries foreigners can’t directly own land or even the real estate. For example, in the Philippines, a foreigner can own condos but not land, in Mexico no non-national can directly own land or real estate and it must be held in a bank trust. In many countries foreign ownership is a hot topic and in some cases it is becoming prohibitive to do so. Get the facts before you take irreversible action. The best place to find out this type of info is from people that you know who own where you are intending to invest, consult your accountant, or legal counsel as they will have professional connections.

3. Type of Property

Deciding what type of property can be the fun part of the process. What type of property suits your wants and needs? How will you know? What is your budget? You need to go and look at many properties and locations within the market you are interested in order to get a good feel. You need to define what you actually want not just for vacation but to live in for an extended period of time. There are many options to choose from in condos, townhouses, villas, standalone houses and it requires some serious thought about your particular needs and those of your potential guests. One of the best questions you can ask is to yourself. How long do you want to live there each year and what part of the year?

Do you want older with more traditional style or a more modern place? By looking at a number of properties you will start to understand the difference in quality and what money can buy. If it is within a multi-family community setting, then what are the associated amenities that you and or your guests have access to and what are the related costs?

Do you want existing or a pre-sale? If it is a pre-sale there are a number of questions to ask. What is the track record and reputation of the developer? What is the timeline for completion? How many homes or units are being constructed? Where does your deposit sit while it is being constructed? What amount is refundable and under what circumstances? What is the payment plan? Do you have a say in the finishes? Are there an upgrade package and what do those finishes look like? As I have asked in previous sections, how long do you want to stay there and over what period of the year?

4. Neighbourhood Location

One of the key considerations to any lifestyle investment is to know how long does it take for you to get there and what it costs for you and your family. What are the options for getting there? Can you drive if you had to or are you restricted to arriving by air?

Is where you are interested a desirable and already developed location, an up-and-coming area (path or progress), or something else? What things are happening or proposed in the area that could change the desirability of where your interested property is located?

In addition to knowing what amenities are included with the property, know the amenities in the surrounding area and specifically within the neighbourhood. This is a critical part for both you and your potential guests. Some people love the lake or beach front and yet others like the quiet of locations away from the lake or beach but close enough for the convenience of access as needed.

Knowing how close you are to the various necessary amenities can be a make or break for you and your guests. What are the modes of transportation in the area and how close are you to public transportation? How walkable is it to amenities, shopping, beach, medical and healthcare, etc.?

One of the key considerations in relation to the location is what would be your return travel costs and the actual living cost for the desired length of time you wish to stay there?

5. Financial Performance & Cash Flow

There are two overall financial aspects to consider when owning a Lifestyle Investment property: personal costs as mentioned above and the actual property financial performance.


You need to understand the acquisition costs, which could include but not limited to legal fees, land transfer taxes, trust set up fees, commissions, furnishing the property, mortgage set up fees to know the final overall price you are paying.

Operational Expenses & Taxes

Then, you need to account for all of the ongoing financial operational costs which include but not limited to the following: property costs condo/HOA fees, annual trust fees, accounting fees, legal fees, mortgage (if applicable), property taxes, heating/water/sewer/electricity/internet (if not included in any condo/HOA fees), home insurance, medical insurance, repairs and maintenance, etc. Also how is the net income addressed in the location in which you own and back in your home country? Is there a tax treaty between the two countries and how is the financial reporting addressed in both countries.

When you are renting out your place you, also need to look at the associated costs: such as maid service, repair and maintenance person because of higher wear and tear, rental necessities such as linens and basics for guests, property management for rentals, marketing expenses, potential additional landlord and liability insurance, business license, fees, and taxes.

Property Management

It is imperative that you hire a reputable, reliable property & rental management service. This may include a repair and maintenance component or these may be separate entities or services, but reliability and reputation is necessary for both parts of the business.

Guest Rentals

Here is the point where you also need to consider who would be your potential rental guest when you are not staying there? Where do your potential guests reside, how do they get there, and what would it generally cost for them to get there? Who is your ideal rental guest? What are the potential rental rates for the various times of year and length of stay based upon your competition?

It is very important to review your property from a guest’s point of view. You need to know what are the most desirable months, then the next desirable months and what months are not desirable in your target destination. Knowing this information will affect when you rent to guests and it help you to maximize your rental rates and occupancy?

Waterfront vs. Inland

On several occasions, I have been asked is it better to own an ocean/beach front or inland property. In my experience owning ocean/beach front usually commands higher rents but there is always a higher cost because of corrosion due to salt air and potential erosion due to climate change. So it really depends on both the financial performance and your personal preference. Some find waves hitting the shore soothing while others find it disruptive when they are trying to sleep.

Exit Strategies

Last financial consideration to address is the eventual disposition of the asset or what happens when the asset is passed on to your heirs. What are the tax consequences in both the destination and your home jurisdictions? How would you or your beneficiaries deal with title changing hands or upon the property disposition. Can the sales proceeds be repatriated or do the funds stay in that jurisdiction upon disposition? Have your exit strategies defined before you buy!

My Recent Discovery Trip

As many of you are aware I just came back from a very successful Lifestyle Investing real estate due diligence trip in Cabo San Lucas and Bucerias/Puerto Vallarta, Mexico. I will be sharing more information in the coming weeks and months as I gain more specific details. If you are interested in knowing more please send me an email expressing your interest: [email protected]

In closing, there are some very big considerations that need to be clarified when Lifestyle Investing whether in your own country or in a foreign country. As for all real estate investing, it is imperative to have a plan, ask all the questions, do your market research, conduct your property due diligence, set up the right structure and surround yourself with the right team to ensure that you are able to enjoy your Lifestyle Investment property for years to come. As a strategic Lifestyle Investor and connected licensed agent, I would encourage you to get in touch to chat about your real estate needs and answer any questions you have about Lifestyle Investing.

Get in Touch

If your are interested in investing in real estate, or looking to list your current home, I can help you form the appropriate strategy and answer any questions you may have. 

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