Hi Joy, welcome to BiggerPockets!

Personally I feel more comfortable being on the over-prepared side (whilst avoiding analysis paralysis) vs. being purely an executor and jumping straight into a bad deal.

I still enjoy painting and doing my own repairs but I've learned that when I do I'm actually costing myself money and then it becomes less joyful to me. 

Just pointing out that based on purely the numbers it is quite possible to get the same returns (or better) making a cash investment than a leveraged one.

All of what you stated for why a lender would look the other way is pure urban legend.

A pure tic structure is rarely used these days because the LP syndication structure is generally preferred to a TIC structured under Rev Proc 2002-22. 

People open Christmas gifts, have their joyful moments, build their families, and generally experience a huge portion of their lives under our roofs- the way I see it, we’ve got the power to affect that in either a positive or negative way, and the responsibility to serve their wellbeing. 

Welcome to the joys of an HOA.

Would you be planning on living in the Beach house, or will it purely be an investment property?

I think the biggest hurdle is the pure lack in quantity of multifamily homes in the area but downtown and the beaches have tons of opportunity for homes to be rehabbed.