The construction guys usually take care of the space the best, and sometimes you can just give them some TI allowance to build out the space themselves. 

My position would be to only allow the new resident if they meet your requirement but NEVER let the one moving out off of the lease until all of them are gone.

Section 8 is guaranteed income on the first, allowing me to scale my business.

All of these tools allow you to pull lists. 

You can probably get a bank account set up that will allows your tenants to make rent deposits. 

Check with your lender what your new payment would be on the existing and what that would allow you to afford on your next purchase.You can still do an owner-occupied loan up to 4 units but if you're using your FHA/VA loan you'll have to go conventional 5-10% down. 

A different approach but it allows us to see what the big $$ items might run when we make an offer and do not waste time with an intermediary inspection.

Based on income, a tenant may only get partial financial assistance with the rent, some may get their rent paid 100%, some get an allowance toward their utility bills. 

I’m gonna be totally honest with you, it’s extremely hard if not impossible to replace a full time 40 hour a week with rental income at least in the shorter, it’s the type of thing that helps you retire a little early and have a buffer in retirement, my grandmother has been in poor heath for years, those properties have allowed us to give her the best care possible, if you don’t already own a home and feel comfortable with your budget and the ability to live in that house for  at least a few years, I’d get started on that don’t even need to over complicate it, find a budget, find a house you like and can see yourself in at least for the medium term buy it. 

Real estate professional status is valuable because it allows us to reclassify these rental activities to active.