But otherwise there's not a whole lot to be done.

You established that your previously owned STR was not manageable due to work stress, so I would question why you would want to add more STR's now while also starting a new business, or at least question if that is sustainable.

This gives me quite a lot to think through should I transition from self-management into bringing on a property manager.Thank you all so much!

Critical Check Points: Tenant selection - screen and choose well; Lease Up - establish a strong rental agreement and make sure the tenant understands your expectations; First Three Months - like a probationary period, check in more often, most problem tenants reveal themselves within the first three months; Lease Violations - swift follow-up and enforcement; Regular Inspections - frequency will depend on a number of factors, including how well the tenant is fulfilling their responsibilities.

Then I'd be on the lookout for established wholesalers and investors in your area that pop up from your keywords.

It’s going to cost you a lot to turn over so if they move, great and if not, you can at least get some interim funds for eventually turning over.

We have a few requests and want to establish one before winter hits pretty hard here :) Our current software (Buildium) doesn't offer any options except just applications.

That's why it can be tough to buy in an area that you don't live in and don't have a good team established in. 

There are ways that an airbnb operation in your home could make sense A) pay over market rentB) profit shareC) guaranteed payment (from an established operator) 

It was tough, but my dad asked if I wanted to go full time to flip and possibly manage rentals for the LLC we had already established.