Charlie... Yeah...mine was a 52 ketch we double handed. 38 is not necessarly too much boat for one person to handle...but the CR has you working out a bowsprit and managing a rather large sail plan for someone almost as old as me and you don't have much experience...my thought is that as a single hander, you don't need nearly that much room and it would be easier to handle a smaller boat that is every bit as seaworthy.
If you go with the CR38...I'd advise to "automate" as much as possible to reduce the work and effort. Boom furl the main, roller furl the foresails, power winch for the main halyard and genny sheets, big windlass with a remote at the helm, wind vane & autopilot.
Of course, you need to be able to manage everything manually...but if you're gonna get a boat at the limits of your ability to manhandle stuff...it is a good idea to be able to do stuff quickly and with the least effort possible under normal conditions IMO. This makes for more complicated systems and added outfitting expense but you won't think of that so much when it is blowing 30 and you need to reduce sail in the middle of the night in big seas. Keep it in the cockpit is my motto!