One thing I think I did learn yesterday is that based on my original calculation, putting the $250k toward the investment portion would result in taxable book on the mortgage payoff of $35,000 because no equivalent debt will be left on the investment portion (only the mortgage debt acquired to obtain the residential portion of our purchased property).

I would prefer to make up the down payment of friends and family and debt for the rest.

The greatest thing you could do at this stage in your life is choose a career path that doesn't involve taking out debt.

The lender said that my Debt to income is too high and causing me not to qualify.

@Jasmine RussellSimilar goals as everyone else here....accumulate passive income to a level that I can thrive without a w2 job.

Only non-real estate debt is student loan and car.

Not my first choice as I was wanting to keep my debt and tax burden lower on my primary residence but I think it’s my best option long term to take advantage of the low rates while they last. 

not employed so debt to income could be an issue getting conventional financing.

Once the debt is paid all I would need from you is a statement or transaction history to show the new balance.  

Eventually I'll want to accumulate cash flowing properties, but harvesting profits now is where my gut is telling me to go.