I suspect selling now would be the best choice, given the market and lack of capital gains (under threshold).Not sure how to calculate this easily – I've tried using the BP rental property calculator, but my numbers are all off since we've already lived in the house 8 years.

Do you guys think going to school for 6 months and getting in a trade for a little to make money asap would be a smart idea?

Part of me feels like I should just keep the cash and make smart BRRRR deals with it, and that I'd be sort of handcuffing myself and penalizing myself by directing it towards my mortgage/HELOC.

You could put that on the line and try and assign the contract, but the seller is apparently (and smartly) keen to what you are up to.

I have my dad money to invest, I'm young, smart and diligent.I'm currently living in Sherman oaks, and doing some office job just to pay the bills.

@Aaron Sladek Smart move going with minor renos I reckon.

I'm glad to see confirmation that sticking to higher move-in requirements is a smart policy to follow.

I always struggle between the choice of faster payoff with less cash flow versus higher cash flow and longer term. 

This princaple is then scaled where professional investors with 20+ units expect to have 1 to 2 units vacant at a time but they have been smart with their investments and that vacancy doesn't hurt them due to the other units being filled.Furthermore duplexes are easier to manage if you buy one closer to where you live. 

One week before the closing we all realized there was no way that we could have moved forward with the transaction because it was too risky.We had no choice but to go back to the seller and renegotiate the purchase price.