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

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

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,).

@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.

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.

Taking the inspiration from the post " How to buy a tax deed at the Fulton County Tax Sale, Atlanta, GA" by Dan M.  

Additional costs like HOA dues, neighborhood maintenance funds, and property taxes over the duration of the build should be factored into your financial strategy.The foundation of any successful partnership lies in a robust operating agreement.

I will give an example, in San Diego at 50% rent ratio (experienced investors should do better than this), the prop tax alone is 20% of the rent.  

This has always been the big downside to syndications - no tax deferral available without starting to daisy chain cost segregations and bonus depreciation.  

Is taxes going to be higher today or higher in the future?