The only thing that I noticed that will hold you up just the same as it can hold up others, is the value-adding equity that you WILL require once you've used up your VA loan limit.I recommend you look at each "deal" as if you are needing to attain at least 25% equity by the time your rehab is done.

My outlook is that I want to replace my current income as much as possible, so that money (in the 401K) is doing nothing for me in attaining that goal.

They also seem safe, have a demographic of higher college attainment, etc.How much does a 2br home rent for with a park view at Riverside Park?  

Your money might be better served assisting you to attain a physical earning asset.

@Tyler JohnsonThank you so much for posting this, even if it was about a year ago.I am currently a Sophomore at my local community college and I just attained my real estate license.  

I wish to pay with time, money and application of my attained expertise in the community of Real Estate investors.     

Although your goals are a bit different than mine, they are certainly attainable.

So, I started studying and figuring out how someone in my position could best attain a house, and these are the options I found:a) Use seller-financing to avoid needing a credit check/big down paymentb) Get my dad or another trusted family member to co-sign onto a traditional mortgage with me to qualifyFrankly, option a) (seller financing) sounds infinitely better to me as I would prefer to avoid banks.

I truly believe that the "American Dream" is attainable and sustainable IF you have the right person on your team.

This is all dependent on data that you can attain, but that is my going in assumption for multis.The older roof is something to seriously think about.