I’d recommend the same if your family situation can handle it.

Obviously the cash flow would go up on the four now paid off units, so that would likely have it's own tax situation change.Is that 400K that was taken as 'cash out' on the original property still deductable since being used in the rental business?

I can’t afford anything in the NY Metro Area at the moment, so I’m exploring areas in:my home state of Vermont (Southern VT mainly)Keene, NYPittsburgh, PA where my brother livesKingston, NY (Upstate NY area/Catskills)North Adams, MA (college town)I’m trying to stick to areas I have some ties to since it will most likely be an out-of-state situation with a property manager.My goal is to buy a 2-4 unit property that is in decent shape, rent the units, and have one unit for myself to come to when I want to get away from NYC.I’ve been running numbers on both the rental property calculator and the BRRRR calculator with varying results.

This is very doable for me given my current financial situation, however after two friends recently expressed interest in moving in, I was thinking of "house hacking" and renting two of the rooms to them to offset some the mortgage.

When I approach someone in a tough situation, I get right to the point but in a way that is not condescending or insulting. 

Find out what they NEED out of the deal and then structure it in a way that solves their problem and creates a winning situation for you too!

I've seen situations where a land is purchased,with building permits on hold for about 8 months at the minimum. 

However, there's an interesting property situation that my mom's living in, and I used it as an opportunity to pretend-crunch some numbers.

I just have an aquaintenance that has a nice system down with air bnb, but I've come to learn it's kind of a unique situation.

So I believe I qualify as a trader as opposed to an investor however I do have some long term investments.Income started with my job (I still work) and birthdays/holiday money.I think I'll wind up being a trader, securities though may be the grey area for my current situation though.