Actually, my plan was very loose, retire from the Army in 2022 then flip a few houses and buy a few rentals which would make me FI enough to not have to work a 9 to 5.

My goal is to generate another stream of income for retirement and am not interested in amassing a multi-million dollar real estate empire.

Question 2: Does it make sense to take everything out of my 401k now to use it on REI considering I am likely in a lower tax bracket now than I will be when I retire?

I live near Cincinnati, so I'm biased, but I believe Ohio is a great place to buy-and-hold because you can find affordable rentals that cash flow well and Cincinnati and Columbus are economically diverse and stable.

Assumptions:  Social security is taken before full retirement age of 67. 

Since I know my personal truck will eventually crap out on me, after the depreciable life of the work truck is done (im assuming 5 years) could I then begin using it as a personal truck, retire my other personal truck and buy a new work truck3. this is a LOOOOOOONG shot, but is there a universe in which I spent MORE than 40k on a truck (or bought another investment property) and was able to move some of the loss to my W2 income to lower that taxable amount.

We dove in head first with it being a second stream of money for retirement, etc. 

Is this a good time to buy or perhaps sit and wait for the market to be more stable?

The owner had lived there for over a decade and was widowed/retired/looking to move with her kids.

The good news is that some landlords that are older and were doing this as a “hobby” or supplemental retirement income may be looking to unload as recent times have been pretty stressful for some.