Nothing wrong with gradual, step-wise progressions

Gradually, science advances and showed that a lot of the diseases people believed were caused by a lack of "fresh air" were really caused by other things.

Margins are usually thin and gradually increase. 

Raising the rents would be gradual as leases renew, with possibly some minor updating (carpet, countertops, paint). 

In the real world, your rental just sits on the market for days, weeks, and months while you gradually slash the rent.

I suspect it was initially rented at market price and gradually fell to $80/month below the other duplexes rent ($30 below per the lease).  

I also talked with him and he wants to work out a deal where I manage the entire park for him for 15% of the gross income ($469K last year), and convert all the park owned to tenant owned homes (he wants to do this).The $5k/month with the actual land owners (also 75 years old) wouldn’t start until the current land-lease is up, so my expenses for the next 7 years would be zero, I’d essentially be managing & improving the park that I’ll eventually own.If I went for this deal, my plan would be:Get it under contract with actual land owner, air-tight where he nor his heirs can back out of the dealThen get a deal worked out with the current lessee to manage his park for 10-15%Convert all homes to rent-to-own (rent credit, etc)Gradually raise rents to marketThe fruits of my labor won’t come into effect for 7 years, but then I’ll be cashflowing like a beast for the next 20 years since $5K/month won’t even be 1/3rd of what actual bank financing would cost.

So they may start high, then gradually reduce it to an amount that is sensible. 

With that being said, I am back to looking for my first investment property, get the experience I need with it, then gradually start building my portfolio as I learn. 

@Maria G. as @Christopher Phillips states, insurance does not cover gradual wear and tear items.If there was an occurrence like a wind storm that tore a hole in the roof, that is now casue a leak, the roof would be covered, but not the ongoing water damage.