We bought our first short term rental a few years ago and self manage.

With delinquent assets, especially ones years delinquent, the 'collectible balance' can be very different than what is promised by a seller due to defensible arguments of Laches and the Statute of Limitations in some states.

Cash, Self Directed IRAs, etc.

If you make a profit the income is not subject to self employment tax.Everything else requires a separate business tax return. 

If you have time, source your leads your self; drive the area you invest in and look for distressed homes, door knock on the foreclosure list, use door hangers when you see a home you really want.

possibly roll it into a self directed retirement account that allows real estate investments. 

This doesn't include PM as we self-manage (we plan to hire a PM once we hit our desired scale)- Cash flow of $2k- Break even occupancy (i.e. 

Opened a HELOC on our primary to self fund our first investment in 2019.

We switched to being treated as an S-Corp for tax purposes around 5 years ago (later than we should have) and it was a really good choice, self-employment tax was trouncing us before that.

Regardless of what happened its going to be an awkward conversation for the tenant to go through, and he will likely get defensive.