This is NOT investment advice and you should check with a CFP or an advisor if you are uninformed about any of this information.  

The same question is true of financial advisors and anyone who works on a commission, really.  

You want to work with an established team to mitigate your investment risks.

I’d love to get involved with the established community and make connections.

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.

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.

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)