They formed all of my entities, prepared my trust and handle my taxes for me. 

But property tax rates can be lower if you purchase properties in this area located in Wise County.

Since beginning I have done one creative finance deal using sub to, one attempted fix and flip, me and my partner own two airbnbs and I have bought and sold many tax properties.

You could still get the tax deductions...rents will likely go up, interest rates will likely stay flat or decrease slightly, Austin has a great outlook long-term. 

.- Our combined after-tax income is $170k annually.- We have no outstanding mortgage debt.Recently, we discussed financing options with a banker at PNC and learned that we might qualify for a HELOC up to $480k, albeit with a relatively high minimum interest rate of 9.31%.

You then, have to Homestead it in Florida for the Property Tax reduction.

Insurance falls under that umbrella - as would something like a tax lien that isn’t cleared up relatively quickly.

However, due to short seasons, and more mild winters, I'm struggling to think even 3-4 years from now that I'd pull anything more than $50K a year in rentals.Bills / property taxes are about $12,000 a year.The thing is, being single, and not really dying to work in this area (small town), I'm feeling rather stuck, as is all the equity.I'm currently not working, but very much want to move back to Chicago, a place I love, and start buying cash flowing properties.I'd suspect I would have about $900,000+ after all is done if it sold at $950K, considering the vast array of other things I've accumulated (wood splitters, machinery, tools, MCM furniture, rugs,).

A DSCR loan will be the easiest to qualify for as it does not require any personal income documentation such as W2's, Tax Returns, etc.

@Taryn Hansen As this is a real estate site I’d have to say rent out the house and keep it and watch it appreciate in value while you earn solid cash flow and get tax benefits.