The biggest problem with 1099 employees, and I use them all the time, is that many are too greedy to not set aside the 30% or more of their check when they get it in to cover the taxes at the end of the year.
I had one guy literally break down and cry a few years ago when I told him I had to 1099 all the money I had been paying him for the lathe work he had been doing for me in his little garage.
He even offered me cash to lose the thing, I had to tell him my accountant takes care of all that and I sure as hell wasn’t going to get audited because he decided to buy a new truck and pay cash rather than set some aside for taxes.
I almost guarantee it got “lost in the mail”.
Sell the company, take the tax hit and move somewhere that is warm and has a beach.
I have one main 1099 “contractor” and another I use sometimes. I put in writing what that means with each check. We actually talked about having him deposit 30% into the business account when he takes his check to the bank. Then I can write him a check to send with the 1099 for the entire amount he deposited. That way he’d have it when he needed it. I agreed to do that but he never went through with it.