If you get yourself an electric pump and a mini 12V battery, it'll make the job quick and easy - there are threads on here covering the Bravo and the type of battery, any problems finding those then sing out. Being able to unload from the boot of your car will widen your possible launch sites beyond what can be reached with a trailer; decent launch wheels should suffice.
My body is five years older than yours, overweight and unfit, but I assemble and launch my Honwave T32 airfloor and 15HP outboard on my own most times from my Vectra Estate or from my motorhome and apart from an incident whilst loading the boat onto the chest high rear bike rack on the motorhome (don't ask!) it's been plain sailing.
I would try things without a trailer to start with and see how it goes before going to the extra expense. If you're going to be taking others with you, then I'd say you'll want the 32 for sure; it speeds things up if you get the crew trained to help with the preparation and packing away.
Good luck with whatever you decide.
so trailering isn't really required if you want total mobility/launching freedom 
sorry Redron 
didn't anyone mention it's a drug mate 
