@Steven Vanderheide
Alright where to start. Well done on the thorough post. I lived in Van for 5 years, the praries for many years, and live in Kelowna now.
First thing I would say, you already know this, just buy already. Second, like Taylor said only you can really decide which one fits for your goals. Having a WHY for your investment helps answer a lot of questions and give direction.
I would rule out option 6 right now. Save it for your second+ property. Get some experience going through the process of buying and owning a home. Landlording, financing, market research etc. You know trades, but that is just the tip of the iceberg with building and there is a lot of other potholes to step in.
I'd rule out the STR in Van due to 1) price/cashflow 2) unfavorable policies 3) Like you said, its big capital locked up for a small property with limited usage 4) STR is either a TON of upkeep(cleaning, marketing, etc) or a TON of expense related to prop mgmt in an already tight cashflow scenario.
BRRRR could be an option in the right location. In Van? Probably not, but in the lower mainland, island, or okanagan potentially ya. Now in my opinion I would still stick to a long term rental afterwards. With your lifestyle you could probably manage a long term yourself from a distance. Just need a good handyman on speed dial. Find a SFH with a suite or suitable that needs an update and away you go. There is no reason you couldnt look at the praries for this also(Saskatoon, Winnipeg, brandon, etc).
'House hacking' doesnt make a lot of sense to me.. if your on the road and dont need a base then why take up that space that could generate income? Doesnt seem to fit. House hacking is one of the best strategies to get started with, if you live there!
Buying a house in a less cyclical market.. Ok, so depending which cycle your referring to? The macro level, as in booms and busts every 8-10 years(supposedly), or the micro aka time of the year. The lower mainland is the least micro cyclical place probably in the country. Very mild winters with little to no snow means homes sell year round. Kelowna is a bit more, but still not bad. You go to places like Edmonton, Saskatoon, Winnipeg.. who wants to buy a house when its -430 C? Not many people. Here is the thing i say about cycles though - ask yourself this, how long do you plan on owning the house? 1 year? 5 years? Forever? If you have a long time horizon the market cycles are much less significant of a factor. Time in the market not timing the market. Buy and get in the game.
REITs - Completely legit option. I started out doing this for the first few years because I was in Van and essentially felt priced out, but didnt want to do long distance. I honestly regret it. I did well for myself in REITs.. dividends were great and I made money. It isnt the same as investing in property though and I would do it differently if I started over again. It could fit your lifestyle so only you can decide.
What did i miss? Remember this is all just my opinion so take it with a grain of salt. Happy to chat about it anytime.
Good luck
