Given the fact that Roth money was invested post tax annually when I qualified, would I need to pay taxes on this money upon the sale of the property, or would this money grow tax free as would all other gains normally made in the Roth outside of a real estate transaction?

But how does one apply and qualify for this 5% down loan??

I'd suggest if you can qualify with just one or two of you, then just have your parents give you the money on the side.

. $300-$350k seems to be the range of house that meets my criteria in this area.The only problem is that with my debt to income ratio (student loans and a car payment) I can only qualify for about $250k.Running the numbers I know that I would live for free and even cash flow a small amount on a property, but of course mortgage companies don't look at this when lending. 

Lease options are only good for 180 days. 95% never close- avoid unless they put up a large down payment, qualify via RMLO - do not exceed 180 no matter what on lease option2.

A pre-approval letter and proof of funds for a down payment don't count for much when qualifying co-op buyers.

@William CollinsMost landlords have a grace period and allow late payments .

I’d like to finance the property to someone who maybe can’t qualify for a conventional loan and secure a loan for them at slightly above or at the market interest rate.Does anyone know how to go about doing this from a legal/underwriting perspective?

@Charles Stubblebine In our market you can easily qualify for a 3% down conventional loan with equal or better terms than the FHA loan. 

Taking action is the best next step since you've already been listening to the podcasts and getting involved in the forums (it's also the hardest :) Since you have a good job, find out how much you can qualify for and go from there!