Bonus if you do any of this in a Roth account.

They do not take into account the revenue from the STR in valuation.Just because you are doing well with it doesn't mean it will work for the buyer.

There's no Airbnb calc tool that really accounts for creativity and its financial value.

Also may need to manage ourselves to account for PM cost.

With a larger organization like iintoo you'll likely be talking to an account manager that has been assigned to working with you.

Quote from @Sam Wilson: We invested via a retirement account.

If you are able to setup a credit card identical to your accounts payable accrual account, it should operate the same.  

if you have an LLC and both properties are under it, you just need 1 operating account.If both are under your personal, 1 bank account specifically for the rental is enough for operating.Security Deposits should always be a separate account altogether.

I operate 14 properties from the same checking account.

A lot of rehab lenders will account previous reno expereince when it comes to terms.