Gradually increase it on them?

To clarify, my thinking would be to live in the 1/1 for a year or two while the neighborhood continues to improve and gradually increase rent.

Him gradually moving his payments to be paid in by the end of the month ultimately may let him get away with a free month of rent.If it bothers you enough to lose a friend, kick him out. 

My goal is to gradually wean myself out of being an employee to an employer.

I would go gradually with the increases, maybe with 6 month leases, till you hit your target rate. 

My parents are suggesting something like having shares such that if they put up 95k for a property and i put up 5k then they would have 95% of the votes receive 95% of the cash flow after all bills (and me being paid out 8-10% for property mgnt etc) and i would get 5% with the opportunity for me to reinvest in the property to sort of “buy” shares from my parents to where I could gradually earn more of the cashflow, principal reductions etc.

Her cost of living has very gradually increased (HOA fees increasing, cost of food, medical bills, etc.)

If it is gradual wear and tear then I would expect you the landlord to pay for it otherwise I would expect them to do it.Example: if this were a door that no longer operated properly is it because the door has gradually deteriorated over 100 years or did they kick it open in a drunken rage?

So I wanted to keep them both and gradually move up if they were good.

I haven't had too many repairs yet so I'm hoping that the amount I've budgets for repairs will gradually build up over time and be sufficient to cover any high expense repairs in the future.