Something to consider is also how up in age is "up in age." Most of the people we have met on the road who are in or near their senior years have gone away from towables and went to RV's. Loading and unloading your Harley, hooking up and disconnecting the trailer, etc. isn't nearly as glamorous as it may seem. Of course, me being me, I rib them for being quitters.
Step 1 is determining what your are willing to spend and, under that guideline, what is your current tow vehicle. If you have a truck and are not going to replace it, what can it tow? If you are going to get a new truck, what do you want to get? This will set you up for the range of trailers that will best fit what you have or will have.
None of us want to see someone buy a 40' Toy Hauler and try to get it around in a 2007 F150.