Sounds like your professional training is a perfect setup for becoming an investor. 

However, I'm not perfect and I always asked my investors to let me know if I made a mistake when analyzing a deal.

It's true you have considerably less ability to vet a renter on airbnb, however, since it's a short term rental isn't the task of finding a perfect renter a little less critical?

Perfectly legal!

A multi unit property is perfect because i can explain my situation directly to you (or whomever the landlord is.)People like me prefer human relations rather than going through a huge corporation that doesn't care about you or your cash.

What are the signs I should look for/track to tell me what direction prices would likely be headed (obviously this isn't a perfect science)?

@Joseph Quinto @Kevin Wells @Dominic Battezzato@Ryan Jackson@Austin Mudd Perfect. 

You should be doing them a service buy finding and marketing their property to buyers that are will to take on the risk of the less than perfect condition of the house.  

I'm not sure how bad this will hit my credit score but I'm thinking it will be bad since I've had perfect credit my whole life.  

(those two white areas are reflections from window)  The floor is still in perfect shape, and has been in for 10 years.