But realized there's no perfect timing unless you are already in the game).

I would be buying into a sellers market in almost any Albertan city.Alberta also worries me as it is known to be super volatile for short periods of time and then sit dormant for up to a decade. 

Everything I've purchased personally, including a recent 4-unit purchased last month, has been heavily cashflow negative initially and it usually takes a good amount of work to get it to cashflow or break even within a relatively short period of time....6-12 month approximately.

**“Kendric, first off, you’re already ahead of the game with your willingness to learn and adapt—plus, having a ‘mishap’ fund shows you’re planning smart! 

If able, speak to them face-to-face at their work, your kids soccer game, church, whatever.

I know a few pro football players that had short careers.

With this scenario we both have skin in the game: His work and my materials.

Quote from @Chris Seveney: @Francisco AvancenaThere are specific lenders who will do land dealsBut of course not as many as traditional real estate.The key will be skin in the game - typically for land because it is less liquid than a home the lender will want to have a lower ltv on the deal I fund land flippers currently in  CO FLA WA ID MT NV AZ OR TX SC GA VA  one thing about land though LTV is lower and RATES are NOT the same as typical HML rates are higher for raw land but its a specialty niche and a business that I grew up in..

I recommend having an attorney draft one that can be short.

We do all our loans as balance sheet loans, so that means short term fixed rates with 20yr amortizations and 20% down.