You're throwing darts at a board with one eye closed hoping to get lucky. 

I confront him all the time on this and he says it isn’t him, even when I have witnessed it with my own eyes.

Things like the asking for the same items multiple times, costs/fees that weren't originally discussed or catching the land contract a bit late in the process give me a bad experience.

Good catch.

Keep an eye on rates as if rates fall you can renogotiate the rate if interest rates fall enough. 

If you don't have income, the IRS will probably catch up with you on filing tax returns for a business with deductions but zero income.However, if you don't care about your corporate veil and don't care about claiming your expenses as deductions (remember, nothing says you have to...), then go ahead --- is my layman's opinion. 

I've had my eyes peeled on Meetup, but no hits on any clubs near me.

While the IRS is not going to check you for the airbnb permit, your city could shut down your operation if they catch wind of what you are doing. 

As I recall, just meeting three of those conditions (and there are several more) moves you from 1099 to W-2.It's been 9 years since I sold my pack & ship store, so maybe that has changed.The USPS is ramping up their competition, so it's wise to keep an eye on them. 

It's stuck in a Catch 22 endless loop.