Holla back, and welcome. There are some great people here that are very helpful. This forum can be a great resource.

I work in operations for Non-scheduled carriers, so I can't be of much help for checking loads, but sometimes I throw my thoughts out there.

As for CPAP, that definitely makes it difficult to not check a bag. I go on trips 30 days long at times, and only carry on. It's amazing how much paperwork you can get done while sitting in a hotel laundry room!