We discuss spending, net worth, and future investing goals with the cash.

The area is way to pricey for my budget so I do all my investing in midwest markets (Memphis and Detroit mostly).

Example - borrower uses loan to purchase a home in a B or C grade neighborhood for 380k, spends 50k rehabbing primary home, uses 200k to put an ADU in the back, appraisal comes back at 925k. 

It's not only the money you'll lose, it's the time you spend (I figure worth $100 hr) and the mental anguish and stress.

Apply for a dimensional variance on the vacant lot to allow a smaller lot and/or setback so it can be built upon.Your best first steps are to sketch a plan, possibly with an engineer's help, then contact the zoning department to discuss your idea with them to get informal feedback on your liklihood of success before you spend a lot of money.

This setup ensures every project stays on schedule and within budget, which is huge in a market where timing is everything.3.

This could be just specific to the real estate industry, but in both recruiting and cybersecurity consultants (hackers for hire), the ones that start their own business/consultancy, are the ones who after spending 2 years (usually exactly 2 years which is when recruiters will message them), the high performer will either 1.

Canadians just spend too much time at home

Only spend 2 hours on it.  

I know you mentioned doing STR, but then you need to spend another $10k+ to get it furnished.