I've looked into umbrella policies but because our primary residences are in NYC and not PA, some companies can't offer it to us.Thanks for any insight!

First off, the bank doesn't really care about who is listed as long as they are the primary listed on the insurance. 

(OR, once I've reached $1-2M in net worth I can cash out and live off an annuity.)Not sure if I'm thinking about that right, but that seems like the two primary "paths" -- not that they aren't interrelated, but it's relevant because it dictates how much of an appreciation play / vs / cash flow play you're going for.I'm 30, I'd love to make "the plan" to hit "the goal" at 50, that seems achievable, but I'm having a hard time wrapping my head around those 2 paths/end goals and how to "SWOT" the routes for achievability.

For instance, lending, syndications, or crowd-funding platforms. 

Hubzu is a very reputable auction platform run by Ocwen, an Orlando-based clearing house for all government-backed mortgages that have been foreclosed upon, i.e FHA, VA, etc.

Wife used to own it as her primary residence before we moved away and turned it into a rental. 

When I first moved to Havelock, NC, I was eager to get my feet wet with my first investment property, after purchasing my primary residence.

The primary determinant as to whether you can buy real estate is going to be your credit score.

Hello Alex,Are you buying a primary home or investment property? 

Thadeous,I had luck with AmeriCU for a HELOC but that was for a primary residence.