I'd recommend you have your financing or cash up front. 

I about gave up when Inslee changed the rental laws here in favor of the tenants, but I was introduced to a very good property manager and have had good luck since. 

If you mixed in cold calling or follow up you'd have better success.

One tenant is moving out, while the other is staying.I have a few questions as the lease wraps up:- How do you deal with the security deposit when one is staying and one is leaving?

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

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

Sometimes taking a break from the corporate life and getting back into REI can wake up the soul! 

Our place sleeps 10 and we don't charge for up to that.

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

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.