I'm getting the sense that your heart is really wanting an STR?

Please know that I realize it is a huge job and huge learning curve and may very well not make good sense, but I want to do a thorough analysis  to determine that (and also what price it may make sense for).  

Speak to real estate agents in the areas you are interested in but also speak to property managers who can give you a sense of the rental market and analysis of pricing. 

-EMD that's non refundable is perfectly fine and makes sense.

Renting where you live and owning elsewhere may not be traditional, but it makes more intuitive sense to cash flow 10k a year off of a 500k investment oppose to racking up a 3k/month liability off of a 500k investment (primary home). 2.

Happy to run through numbers with you to see what makes the most sense.

That said, we’ll go anywhere in the US where housing is needed and multifamily development makes sense.

You can go there and ask any and all questions you have.It sounds like you are leaning towards continuing to run your own bookkeeping which I think makes sense considering you have a few properties and just started.Bookkeeping for rental properties, especially when rehabs are involved, is more complicated than most people like to believe.

We are no Boy Scout either, but in a relative sense they are different worlds.

When you bake in those expenses renting makes no sense unless the cash-flow is insane.