The deals are out there OP but they are very unlikely to fall into your lap.

Are you able to strategically reduce costs or increase rents or generate any other sources of income from the property (garage rental, coin-op laundry, etc). 

If that lease is renegotiated every 5 years, it's not really a 99 year lease, I think the OP means there is a provision for rent adjustments every five years and that won't just be an open ticket to charge at a whim.......otherwise the bank would never have taken it or built on it.

I’m an ops manager for a tree company out of the western burbs however we service all areas of Chicagoland.

Looking to chat about Co-ops, and how to take title with one.

The modern day coin-op laundry lol 

Hi Darren,This type of fee is very common for co-ops in NYC.

I'm in the process of getting a 50 unit multi family Co-op under contract.  

One thing that is very certain is that it will be much higher in 25 years (op’s timeframe) - 10x or so with zero effort while he is busy earning his active income.

I hear what you are saying; however, I do have access to a good team through a friend as my OP mentioned, so I do think the 30-50k houses will cash flow nicely.