What about if renter 2 states they feel uncomfortable with living with potential sublessor?

If they posted my the same cheque (check) on the day the rent was due and it arrived several days later I'd consider the rent late.I'd expect bank transfers etc to arrive into my account the same day the rent was due.Again, thinking purely practically if I received notification each month the rent was paid on the due date and it arrived in my account the next working day I wouldn't be inclined to make an issue out of it. 3 days or more is a problem, less is a transactional delay I can live with, especially if it's routine and reliable.

I feel like this puts you at a significant amount of risk, and carrying that much debt once you have acquired 5 or more properties makes me uncomfortable.

If you feel uncomfortable, just have the title company hold it instead of the listing agent or the seller's attorney.

Your property manager can help decrease these cost by finding quality tenants and doing routine inspections.Feel free to reach out for any resources. 

Maybe instead of buying your first investment with an FHA loan in an area you're uncomfortable living in, it's a sign that your capital is better allocated in a joint venture with a partner who is willing to be the boots on the ground doing the rehab.

I would feel uncomfortable with anything less than a year, but everyone has there own risk tolerance.

Definitely takes some courage to get comfortable being uncomfortable and put yourself out there.My first thought is why wait? 

A routine will be your best friend!

The problems that come up during our everyday business dealings may seem routine to us but could represent a major pitfall for someone who is not used to dealing with them.