My main concern is how my friend will be paying income tax from the rent - need 1099 NEC , but who will issue the 1099 NEC ?...

How they work that out between themselves is not your concern.2) You say you don't want to manage roommates, but you already were.  

Purchasing real estate while having a nothing more than a leasehold interest in the land put any loan made into a “no man’s” land as far as compliance is concerned.  

My only concern there is... finding a deal(s) to reinvest that 1031 money before my 6 months is up.

Thanks for clarifying some of my concerns, this makes me feel much better about the process.

Now to your point I agree we have some major issues coming up concerning inflation and having a stable economy. 

I do plan on getting a backup generator but there’s a one year backlog ughPlumber is pushing for me to switch to a new propane heater to heat both units.My concern is running out of propane and having the pipes freezing...Someone suggested to me that electric baseboard heaters are a good choice and cost effective.

For context, we are stable income-wise, so no concerns about a job loss or injury preventing us from making payments.

A very simple but big concern that arises is an exit strategy - what if you purchase the property over market value, and suddenly need to get out.

honestly, its not clear what you want vs. what you are "concerned will happen..."