Tons of red flags but there’s also a lot of nonsense in here about if he had money for the new business he wouldn’t need to declare bankruptcy. We seen this a ton during and near the end of COVID in restaurants. They closed for a week or two and suddenly are back open with the only thing changing is the name of the LLC on the business license.

Just because a business goes bankrupt doesn’t mean the owner still doesn’t have assets/cash. In fact it’s many reasons the business does go bankrupt because the owner pays themselves too much or the business “buys equipment” that in reality ends up being the owner’s. Depending on how long they’ve structured this and the business’s cashflow over the past years, it’s very likely the assets gained from the business won’t be clawed back by the court.

Get a real processor that uses an Authorize.net gateway and stop using this third party aggregator shit.

Stripe isn’t the same as something like Payroc and they’ll use every reason to screw you out of money.

Parts - $xx.xx
Labor - $xx.xx

Nothing says you have to give the part number. Why not give an internal part number unique to you?

we don’t have a specific time off policy

Now is the time to implement and and consider a lesson learned. Going back on an employee is wrong no matter how you justify it to yourself and is a quick way to lose an employee (or more if they also feel you screw him over).

What you haven’t stated whether it’s “vacation” or “PTO”.

15 days of PTO at 5 years is pretty slim especially if you don’t have separate sick time.

It’s also wrong for you to try to go back on him, that was a conversation that needed to occur at the event, not a month/six months after.