Now I want to get to the promised land and cut my day job. 3 years ago I bought a vacation home near Cape May, nj for 155k(cash), put in 60k in rehab and just got a cma for 268k.

There's moratorium's across the country on evictions and the cutting off of utilities for non-payment. 

An umbrella policy is just as good and can cut out some of the headaches.

Then you want to incentivize your PM towards finding tenants that are likely to stay long-term (this weeds out college students and recent transplants and divorcees), conducting regular inspections, and maintaining tight standards over the properties (regular spot checks for grass cutting, timely correction notices, etc).

Also, if it's a legal building, there are tax records somewhere, so dig a little harder.If all else fails, post the deal here, either with a cut for yourself added in if you're trying to help yourself, or without if you're just helping him.

It's referred to as illegal "tying". 

Much more so than by cutting corners and saving $500 on XYZ DIY job, so finding it cheap means you can save more time and spend money in other areas.

Driving maximum rent is usually tied to condition and location, but there are other factors...like the current market.

Hoping this helps open your options, but if you do insist on putting the 20% down you can go get a HELOC to access some of the tied up cash. 

So if you can cut that down by $1000/month, it's like making an extra $1000/month.