Should I venture into these unknown waters?

Wanted to check to see if anyone is actually using bitcoin/crypto in their real estate ventures.

If not then you should google (Private flood insurance) or (Lloyds of London Flood Insurance) you can also check out this article that Investopedia did on flood insurance.Best of luck with all your ventures. 

Sure it's easy to not lose money if you buy and hold and never sell a property.  

Start with how much do you have to lose.

Another possibility is renting it to a business venture that will run a stable operation.

You’re losing sleep while she’s sleeping like a baby.

In a market down turn, condos are the first to lose value and the last to regain value in an upswing.

Joint-venture?

You can move into the rental suite and rent the main part of the house.If you buy a rental, you need 20% down and because of that won't have to pay CMHC insurance.As for purchasing and selling in 2 years, you will lose money.