The desperation is not something that substantially contributes to a good deal.

I have goals of contributing my engineering/project management background to creatively house hack and streamline growth potential.

Even if I did buy it below market, I do not see how that should be a contributing factor in its fair market value 2 years and 10 months later.

When that time comes, am I able to use my retirement account to purchase my house from myself at less than market value (being the note amount), allowing the retirement account to own the property in full and collect rent into that account; In addition, still allowing me to maximizing contributions each year?

It's a relationship, notwithstanding a business one.How much did you contribute towards the renovation?

@Brian Eastman  thanks Brian I knew you could shed light on this.. and that is my sole contribution to this thread.. bring in the expert !!!!

Did you contribute the money to the LLC and then purchase the property in your own name?

From bottom to top it goes:Basement + 1 Apt with oil heatCommercial Oil Heat3 Apartments Electric3 Apartments ElectricI'm buying the building with only 3 tenants and know the electric heat may contribute to the reason why its not being filled. 

Another aspect to consider is that once your equity grows to a certain point it is generating the entire return and the property is contributing nothing.

I’m guessing I’m going to lose my buyers and they were good.. conventional loan 46k down offered me 2k over list price with no contingency or seller contribution.