He ended up taking advantage of me saying 'yes' to every request.

The model simply doesn't work for cash flow focused investors. 

I was 2 days away from being late, and potentially opening myself and business partner up to fines of $591/day.

Look up mortgage brokers in your area and do the same thing.

They are in Meet up and EventbriteSee you thereLuis MMP

Plus, with your tenant experience, scaling up with more units under one roof makes sense!

Obviously, it depends, but how would you divide up that money?

It is difficult to maintain, it scratches, it warps, it stains, it needs to be cleaned with cleaners made for wood floors, pets tear it up, it transfers noise, it shows wear patterns, etc. 

A couple of them are big time investors these days with over 40 houses each and have moved up to STRs and commercial properties.Find someone that will share their opinions and suggestions and it'll help keep you motivated to get through the starting period. 

You need to set up marketing to find these leads which takes time and money.