I looked at each rental I purchased as buying back my freedom one house at a time.When buying and refinancing into traditional financing with a W2 is easier than you think.

And it's not going to take too much of a pop in mill levy for you to see a hurt to your ROI.But all that being said, at the end of the day, that kind of revenue off of an asset in a traditionally appreciating market is worth a long look - either to 1031 into or to refi your current and simply buy it.

I do not want to work a traditional job my whole life.

It is not Income, it is typically a combination of "equity" (CIF - Cash in Fist) and "debt" (loan - HML, PML, traditional bank). 

If you find a good one, it will help your situation which doesn’t fit in the bullseye of traditional mortgage.

Will you have some trouble qualifying with a traditional lender?

I do not think any of them desperately need a large check(like they would get from a traditional sale), but I would want to pay them for the house within a year or earlier if possible.

Even though I am still employed and actively contributing to my 401K can I not rollover to a Roth IRA / Traditional IRA?

You guessed it: the financing.I'm pursuing buy-and-hold, SFH.I don't have much of my own $$ to throw into the pot, so here's what I'm thinking:- Figure out about what a house would cost (I'm told to expect ~$200K - $250k)- Assume a traditional loan, and needing 25% down- So I'll need to raise ~$62,000 for the down payment- I approach friends and family, network with potential investors to raise those funds- Bank supplies the loan for the remaining ~$180,000Something like that.Should I speak with a real estate attorney before approaching those potential investors?

If you don't hold up your end then they would be able to take the property back.If they still have a mortgage and you don't have the $$ to purchase or get a traditional loan then I would HIGHLY recommend that you sign a 1 yr lease with the family member which would guarantee them an amount every month regardless of the income generated and the balance is your profit.