If you're negative and looking at potential deferred maintenance I'd sale it and enjoy the memories. 

There are some markets that will write both together and if affordable, that would the way I would recommend going.   

As Judge Judy says, "if it's not in writing then it didn't happen!" 

Also, running a flip with no money and hoping you get a good return with all the other stuff going on in the background starts to add stress, and you end up not enjoying it.

Because this is the business we've built together, we enjoy working together, we each have roles that reduce the work load on the group and personally I like that the risk is spread out.

If not, I’ll write it off as a loss.

Before listing it on an STR platform, I need to make some improvements to my current home.How can I maximize tax write-offs for these improvements?

Write as yourself, not a company, and tell them you are trying to buy your first property in your own backyard and would love to have a conversation whether they want to sell or not (they probably know someone else).

I hope you enjoy small towns that lack diversity.I am sure Dayton has some real estate meetups.

Totally agree , and when a home inspector looks at a house built over 100 years ago and writes a report based on current codes .