I asked when the other person will retire.  

I had another person speak highly of New Western.

I tried to create rapport with the owner over the phone but waited to present my real agenda only in person.   

Some high-end STR's (like in Joshua Tree) do use professional models, but for your market and property type, I’d suggest removing personal photos and focusing on the space itself, so guests can imagine themselves there, which is really what you want.You also have 81 photos, that’s too many.

For me it boils down to more of a personal decision - can I afford two homes, do I want to have two homes and the stress of it, or just take my money out of one and put it in another.

Nice to connect 😎Its in Joliet - Cathedral area I hope to meet you in person as well?

Maybe we can help a lot of people on this Bigger Pockets platform.So if you are an experienced investor, flipper, or buy and hold person?

Either way, $600 in cash flow should actually help your personal DTI if you go for conventional financing on a primary again. 

One-person rental units are in the highest demand, and co-living directly appeals to this market.

I wouldn’t personally recommend it, as office vacancy rates are currently quite high.