I think paying off a loan with a high interest rate debt and adding to the principal is one way to stay liquid within the property. 

Hey Connor, welcome to BP! 

Alternately, if you’re going to do this at volume, and you’ll have to since margins here are thin, I would attend some of the lender conferences.

Plus we have 7 offices around Orlando and looking to acquire more next year.

If the rate is reasonable then it may make sense to try to save fast to get to the 3.5% down payment on a double or triple - househacking may allow you to increase your savings rate and pay down that loan even faster.As for estimating costs, closing in NY factor at least 1% of the mortgage amount for tax, plus $1500-2000 for lawyer, title and fees, then the amount required by the bank for escrow will depend on the actual property taxes and insurance.

I would point your accountant to Section 469(g). 

I have just over $200K left of owner-financing, but I'd like to obtain a cash-out mortgage/loan of $500K (ideally) to be able to pay off the previous owner and make some repairs, etc. 

You've definitely come to the right place to build connections and learn, but you want to pair these forums, books, and podcasts with in-person real estate investing meetups in your area.

Worst case with auction you get to live in it for 2 more months and don’t have to pay to sell.

Quote from @Chris Seveney: Quote from @Hector Espinosa: I don't really have many lesson to share this year but I hope next year I can have more to share.