So I’m thinking it’s better to replace rather than repair.

My agent is from Atlanta and he doesn't seem to think I will have any trouble renting but I am truly a little nervous at this point.

Remember that you need to think like your partner - what do THEY want out of the deal?

I think  you have given yourself the best advice " I would love to join in on any BP groups that do OOS deals (I have proven time management, attention to detail and paperwork organization skills in exchange for getting to learn alongside some REI masters)."

I work full time at a local Chip( hint people think i work at Stadium) company as an Telecom engineer for last  20 years and still love the work i do and hopefully they don't fire me.

It's a chicken or the egg thing- no one will book your property as an STR if it isn't furnished, but I don't think you can capitalize those expenses until it's in service. 

I think some people sell their judgements to collection companies for a very small amount but I have never done that. 

As far as planning, once you get into it, you will realize you dont really need that much to start buying houses, but I think it is a good idea!

You think losing a $20k EMD when you don’t close sucks, but the seller might get hit with a $100k tax bill when you don’t close, on top of losing their own EMD. 

I'd think return of the security deposit would be voided since she is breaking her lease.