We have sold (tax free), kept as long term and/or short term rentals as well.

It’s definitely smart to evaluate the tax and cost implications of your funding options.

So the question becomes based on their individual and personal tax situation what is the estimated tax burden they'd save? 

If so, there are no transfer taxes due. 

Tax-Free Exchanges: While 1031 exchanges aren't available to SDIRAs, the tax deferral within the account means you can sell property and reinvest proceeds into new opportunities without immediate tax consequences.

After closing, work on increasing your income, reducing debt, and preparing for a second mortgage.

Thanks again for your input, and I'll probably reach out as I get further along in the process.Hi @Edward Zachary Samperio, the regulations aren't that difficult and I'd be happy to give you a quick rundown about the density limits, hotel occupancy taxes, permitting, etc.

Any existing debt?

In that case, you’re living for $2,000 a month—while building equity in the home, benefiting from potential appreciation, and taking advantage of valuable tax write-offs!

If you have a lot of equity and little cash flow, you should consider accessing that equity to use elsewhere.Another factor to consider is your interest rate on the debt.