(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.

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

There are way too many things that are different from a condo than a traditional MF.

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.

You wont make as much but you'll each make 10k-15k off it, with no money needed up front, and then you can put that 10-15k towards another property and use more traditional financing with a downpayment on ur own.

Consider property taxes, utilities traditionally paid by the owner in that area (water, trash, electric, gas, ...), repairs, maintenance and landscaping, costs to service the loan, etc.If your friend would become your tenant, would you be willing to raise the rent on her? 

Sub2 on a heloc is probably trickier since they can be called even easier than a traditional mtg, aside from the due on sale clause.

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

Traditional financing is probably out because of debt-to-income ratio.Anyone know the pitfalls of getting a HELOC in New York, or have any preferred lenders?