Hey Matt, when it comes to HELOC's the monthly interest will start to eat up profits after a while. 

Termites etc will eat away structure.

Extending the parking area right up to the house, means no weed eating, just some weed killer a few times a year.

Hiring a property management company will eat away roughly 10% of your rental receipts; however you won't have to worry about creating a contractor list and you may not have to deal with calls at 11:00 at night.Upstate NY is also an option.There are a couple of real estate networking events that meet in NYC.

They eat up your cash and really don't provide much value in my opinion. 

I do need to create a nest egg which I am working on. 

Heck, I even find joy in it when a squirrel eats a hole through the kitchen ceiling, the fire alarm blasts for no reason, and the tenant's kid secretly turns off the "do not turn off" switch to the heater, necessitating an emergency call to the electrician.Three years after retiring from freelance writing, I'm looking for my next act.

Besides begging and pleading and eating crow, not much more you can do.

Would love to have the opportunity to get experience without one but I've seen, in other industries at least, a chicken and the egg problem. 

Once you have a nice nest egg, you can attack this from a position of strength.