When you withdraw that $13,771.30 from your IRA it will be subject to your ordinary income tax, the same as if you had earned that money.This may seem like double taxation.  

There is a growing number of Canadians - et Québécois(e) - here who can be of assistance with any questions specific to financing, regulation or taxation in Canada.

I looked around but did not see anything specific regarding the order of taxation. 

The seller is open to owner financing due to not having to pay all of the capital gains tax at once, but rather pay it over the life of the loan to me.I would essentially be leading him to believe that he would be able to pay the taxes over a period of 10 years, and then turn around and force him to pay the taxes in full 6-12 months later when I refinance.

The goal is to set up an investment structure that optimizes the level of taxation given the aforementioned context.

(For example, what if I die, what if I live too long...) and a way to avoid taxation.

It is very easy to manage with a yearly taxation of $800 (at least in CA).

Perhaps pursuing a degree in accounting to supplement your MBA could help you in the long run, especially if you focus on taxation and managerial accounting.

In accountant talk: Acost segregation study identifies and reclassifies personal property assets to shorten the depreciation time for taxation purposes, which reduces current income tax obligations.

The rental property market in NJ seems like a real stinker given the taxation and landlord tenant policies over there.