One sale can be worth 10-20 leases or more, personally I would rather work really hard to sell a few properties if I was just getting started.

I have read and watched a lot about it so I have surface understanding of how it works, but I feel that I do not really know much about details like tax implications , among other things that could influence my decision to start investing.

I'd like to start small with 1-2 STR tiny house(s) or other less expensive "alternate housing" options (yurt, airstream, etc).

This is not me trying to start something.

I found this one literally from passing though the area and seeing that they had started some sort of reno with a dumpster out front.

This can be a real money-maker, but you need to know what the risks are, how to mitigate them, how much to charge for rent, insurance requirements, and more.Honestly, the couple relocating sounds like the best option.Here's a tip: don't reject applications just because someone else started one.

I am starting to think about selling the unit since rent is $2,300 and my P&I&Taxes are sitting at $2,100.

In essence you have to prove your house isn’t worth what they say it is worth – and since they started 15% below market – you have to be able to justify the argument that your house is worth (say) 25% less to get a 10% reduction in your taxes.  

I'm new to the forums and starting to dip my toes in Landlording this year.How should I analyze my live in condo owned for 9 years.

These forums are a great place to learn and meet people, whether you're just starting out or you're a seasoned investor.