I wouldn't spend any money on a new converter and the cost for R&R of a transmission for that (think 8 hours labor, plus parts, save it for the what-if instead). Use tow/haul and use some common sense and you'll be fine. I've hauled for years with my 6L80 transmissions and haven't has any issues.
DO the thermal bypass for sure. Also make it a habit to get the trans serviced every 40k or so. There are a lot of factors that go into killing a transmission, so control what you can - keep it cool, keep it clean, keep your right foot out of excessive throttle (unless necessary obviously).
Based on the inspection, I feel you got a clean, well cared for vehicle. Use the info provided to save up for needed maintenance items that will be coming due in the next 10-40k miles. As for the potential A/C failure, if it's still holding pressure after 9 years and 40k, you're probably in the clear I would assume.
Also, DO install a RANGE Device, or get a tune to shut off AFM. Make it a point to change your oil every 5k or less and your engine will appreciate it.