If I do contact him, what should I say?

I financed the deal with a conventional loan and bought down the rate from 7.75 to 6.25.

To add to your argument I suppose the tax implications are better with RE too bc theres a capital gains tax ceiling of 20% vs standard tax rates for IRA withdrawals that are potentially much higher.

Jung,Welcome to the BP forum its a great time to start as mortgage rates fall and home prices still priced well in many states.

And it's very pertinent to today's environment because it doesn't look like interest rates will be coming down much, if at all this year.

Some lenders offer discounts to return borrowers so maybe look into both flip and DSCR rates when finding a lender. 

That strategy, however, is going to take a lot more up front work than just posting a bedroom for rent for $900/month (or whatever the going rate is in Richmond) on airbnb and FF.

Have you searched your county site to identify those that have bought land in your area the past few years and then contacted them?

I also wouldnt let your mom go into 2nd position on an investment property with any sort of restructuring; it doenst sound like she's in a position to risk being wiped out.Overall, though, if you want cashflow on the new property but cant achieve that after a refi into a market rate loan, it probably makes more sense to just flip it, pay off your heloc and your mom, and use the remaining capital for the next deal.

I've also held of holding properties in individual LLCs that are owned by one S corporation, which allows for a 60 / 40 split between ordinary income (regular tax) and dividends (capital gains tax rate).With the goal of minimizing taxation and liability protection, what would be the recommendation from more experienced people here?