I haven't read all the posts so sorry in advance if this has already been said.
It's not uncommon for "the older generation" to lose the medical or for whatever reason be "unfit to fly". I'm sure it wouldn't be difficult to find an instructor who would be happy to go on flights with you. I've done plenty like this and it's actually a pleasure to fly with someone who already has so much experience and we can just get on and "go somewhere" in stead of bashing out more circuits!
I'm not sure how much a medical and license renewal will cost, but for the same cost you could fly with an instructor (about £20 / hour) for ages! OK, an instructor has to be available, but the guys I fly with are invariably grateful for being able to offload some of the work onto me and leave them to just enjoy it.