Hi @Dave Bopp,I obviously have not seen your finances so this is in part speculation, but if the lender you spoke with did not include rental income from the hypothetical property you are looking to purchase in the math (most wont), then it's entirely possible that a traditional mortgage is still an option.

@Michael BoyerIf you wanted a Roth, you could convert your Traditional IRA funds into Roth.

I'm having difficulty securing traditional bank financing due to large student debt and being a 1099 employee, so I'm just trying to brainstorm.

If your lender is citing Fannie information, that is a traditional loan to your personal name.

That said, I'd like to establish a repore with my new tenants and introduce a platform that makes the rent payment process easier for all parties.  

If the city could prove that the home was either not lived in for a year or that it was used for any commercial use then they would deny the certification and traditional residential financing would be a lot harder to get.Something else to keep in mind is that if I did change the use of the land I would need to bring the standards of the lot up to today's standards.

Most traditional lenders don't offer this type of product.

Unless things have changed in the new year, there are also some 5% down traditional mortgage programs where you won't have to deal with FHA requirements. 

That being said I estimate there is about 30-50k worth of work to bring it up to the level of the comps in the area.My wife and I are not rich but we have no debt, we have 250K in our retirement, I have a pension I am vested in and we have about money tied up in investments that we can if need be make liquid.I have been working with a mortgage broker friend and he says we are golden to purchase anytime but I don't want to go the traditional route with 20% cash and here is the strategy question.  

Assuming nothing has been upgraded for 80 years it will definitely be a challenge to get tradition DP3 and REIGuard may actually be a good option.