Debt paydown vs. scaling

[Jake Salisbury]

Hello all,

Warning, this question has many parts.  My girlfriend and I have been going back and forth on this question and would love to hear what the BP community thinks. Our goal is to have financial freedom, at least $10k a month from RE investments in the next 10 years. We are struggling to know which direction we should go.

We currently live in a condo that if  sold in this market we would net $80k. It is an older property with new condos being built within our communities. Our first question is, should we sell this place now and use the $80k for a multifamily property or hold and use for a rental property. It would cash flow as a rental property but not as much as a multi. We  currently have enough cash on hand to invest in another multi family without selling this property. Additionally, by September we will have lived in this property for 2 years. Is it worth waiting until September and hope the market is still as strong or take the hit on capital gain taxes and sell now.

Secondly, if we do hold this property would it make more sense to prioritize debt paydown (instead of investing in another property, put our cash towards our mortgage payment and have it paid off within 10 years. Then we would be profiting a clean $2k a month from just this property alone and still have money for a down payment for a house hack. 

Thanks all!