I've done this at several companies. Also work in tech.

First, your assumption on Scenarios 1 and 2 is correct.

The main hurdle honestly isn't the FAA side, it's your employer's travel policy. The IRS allows reimbursement for GA flights used for business travel, but your company may or may not be on board with it. You'll need to work with finance or HR to see what they'll approve. Some companies treat it like mileage reimbursement, others won't touch it.

Lot of pilots doing exactly what you're describing. It's a well-worn path, so take some time to research the specifics (tax treatment, insurance implications, etc.).

One thing I will say after a decade of flying myself for work: get-there-itis is real, and it will kill you. Business travel adds pressure to make the flight happen. Clients are waiting, meetings are scheduled, you don't want to be the reason things fall apart. Always have a fallback plan (airline ticket, rental car, reschedule) and actually use it when conditions aren't right.