You can't handle what you've already got, so why would you take on another debt?

In my case I work with a local title company that also handles the exchange.

We have $20,000 to put down and will handle all of the financing and rehab.

Regular PMs don't handle these properties.

Anything you have, 99.9% of the time Harry can handle it.

I wonder how other people are handling these struggles?

I do have a CPA that handles all our taxes.If you are providing services, like tours, cooking meals, driving folks around, cleaning during the guests stay, then you will fall under schedule C and pay the taxes.Leaving things for folks like a welcome basket, coffee, bikes etc does not do this.

This should be a passive business for you and the manager should handle everything.

Any investor could do this and if they didn't want to manage the STR side they could use a team to handle that too and make it passive.

Second, in discussing the matter with the Tenant, I tell the Tenant that I don't agree or consent to the Tenant moving out early and that we will handle the matter according to the Lease.