one repair will eat that 250 a year profit on your door.

If I were to research properties around my area, and get a feel for the market, would it be smart of me to take my nest egg and try to find an investment property around here when the market is low, so I can do a buy/hold/sell strategy?

I guess that goes back to eating an elephant 1 bite at a time.

You are 3.5 years from the PMI drop off and its almost guaranteed you will have an unexpected expense/possibly a large one, that eats into your cash by then.

my modest salary combined with 6500/year in property taxes and my conventional note eats up a bulk of my DTI.

I would think the benefit to lending to multiple people would be that it minimizes risk in case something goes wrong with one of the flippers.However, if you developed a solid relationship with a borrower and they have proven themselves to you many times in a row, would you put "all your eggs in one basket?"

It's against my personal code to lie but I will admit I have lied (ie told mom I didn't eat the cookie and others) and am not proud of it.

Vacancies, repairs, management and other costs will eat that $300.00 plus more.

I don't think 401k are all that bad, you are still relatively young and what you put in now will have plenty of time to mature to a sizable nest egg.

looks like a good deal rahman on paper, couple of things I will look for is water bill 100$ for three units is very low that bill alone can eat into your cashflow.check the area out as Ali B is suggesting, if its not an OK area expect higher turnovers, vacancies.