They get a higher return since they are covering housing cost, have the $250k per spouse primary residence deduction in gains, is a savings account, higher leverage position, lower interest rate possible, will pay more premium for location, etc.House might be overpriced for REITs but not for home owners.  

I have a large lump sum saved in an investment account for down-payment and any additional costs.

Account ClosedAdding your property manager as "additional insured" is standard practice and beneficial for you.

However, I got caught up during creating my listing because it looked like I needed to have another account (Stripe?

We also didn't take into account the slant in the floor either. 

It forces me to call VRBO to reset the account but luckily they are easy to get a hold of and fix.  

A great deal of accountants work with out of state clients.

Also, make sure that they have money in their accounts in case things don't go as planned.

If it concerns you that much, adjust the purchase price to take into account this added risk. 

I think most successful investors would tell you that, while you need to take tax into account in your decisions, you shouldn't make a decision based on that alone.