1) you are NOT too old, as you will have gathered from other posts.
2) you may have strength issues, but your health
and strength will probably improve as you go along.
3) there are ways to get around strength, for the routine stuff, by power winches, on sail boats, if nothing else. A power boat gets rid of many "strength issues" and should definitely be considered. (I am a sailor, but understand this)
4) where strength is an issue is in the unexpected things. Like moving a boat around a dock
by yourself when it is blowing. Like lifting a dinghy
. Like going up the mast by yourself. Etc. Etc. Etc.
5) stamina is also a big concern, even bigger if you plan on singlehanding
. Don't underestimate this. Exhaustion breeds bad mistakes
. You may want to develop a list of friends who might like to accompany you on anything longer than 24 hours. If you think ahead, there won't be too many legs longer than this. This life really IS much more rewarding when shared.
6) both monohulls and multihulls should be considered. I have lived on a mono for 19 years, and a cat for 7. My own personal opinion is that you would be much better off on a cat, but that you should be wary of a big cat. Cat's are safer, not for the reasons that cause most arguments, but because you are less likely to slip yourself, or scald yourself, or all the other things that can happen when you are heeling, if you aren't pretty nimble; and you have told us that your strength and condition is a bit compromised, so I imagine your mobility might be, too. Cat's are much bigger boats than the equivalent sized mono's and if you don't realize this, you might really bite of too much too chew. I can easily singlehand my 45 foot cat ( I am 62), but I have been at it for a long time. A whole lot bigger would be pushing it, even for me. But, don't forget, if things get to be too much, you can often simply slow down.
7) every harbor has at least one boat that seldom moves because it is really a bit too big for its (often singlehanded) crew.
8) I had a dog aboard my 33 foot monohull
, and it greatly improved the quality of my life...made it much easier to meet other people, too. There is no doubt that it will be a hassle, but nothing in life is free. In my opinion, pay the price
and take the dog.
9) visit your local marina, sailing center, or yacht club and tell them what you are trying to do. Many will tell you not to (after all, most of them aren't trying to do it, and that affects their opinions). Ignore that, but try to get a feel for some different types of boats.
10) charter a boat somewhere, at least with a captain
, maybe with full crew. Before you charter, tell the captain
what you are up to. Try to find someone sympathetic and patient. Maybe a bit older. Maybe a dog lover. Maybe a teacher. You will find that person will probably turn out to be an enthusiastic and encouraging mentor. Might even give you more truly useful instruction than the formal stuff in a sailing class.
Finally, good luck, and keep at it during the moments (they will occur) when you feel discouraged or simply insane. They happen to all of us, young or old. You have the advantage of handling them with more maturity than most.
And, do take the dog.....and probably on a smaller boat than you first might want.