I know it seems like a tough task, but can you spend a few more months or a year while you continue to learn to really tighten the budget or find ways to earn a little extra to start from a stronger position?

If your leasing application process is thorough and well thought out, and if your lease agreement has been well drafted by your local attorney and if it includes clauses that permit you/your property manager enough latitude to maneuver and anticipate undesirable tenant behaviors, both actions and inactions, and you have operational processes which align with enforcement of your lease, then you've done all you can do to reduce this inherent risk of an undesirable tenant.  

Energy Efficiency ImprovementsInstalling energy-efficient windows, doors, insulation, and HVAC systems can appeal to modern buyers who want to reduce utility bills.

I’m sure he feels like he earned that money because of how much time he spent going to different sources supposedly.

The account does not have to be an interest bearing account but if it is, then a portion of that interest earned has to be returned to the tenant annually.

And IMO that has been decades in the making.I saw a recent survey of 4000 Gen Z and they said thay would need to earn 270k to feel financially successful.

Just reduce there rent by $5 and they will be happy to do it.

Remember that the leveraged purchases are not going to add significant cash flow immediately and borrowing against existing properties will also reduce their cash flow.

It might be a situation where you are digging a manageable hole that you can work and earn your way out of, but be honest with yourself.

After five years, I am willing to buy the other owner out or they could stay in and continue earning and enjoying the property.