I hadn't seen this thread until now, so I'll make my contribution seeing as how I too have been wondering when age/health will affect how/if/when I do certain things. Turning 60 last year definitely put me in a thinking mode given how quickly the past ten years have passed. My guess is, I'll feel a bigger difference during the next ten.
I am physically capable of doing the same things now that I was 20 or even 30 years ago, and I am thankful I've been in good health, at least for the most part. I too used to be a perfectionist, but as the years have gone by, that is becoming less the case. I'm guessing that having a child come along so late in life has changed a lot of that. Being 60 with a 14 year old living at home definitely changes things, but in a good way. I honestly wonder why I even keep my Hatteras at this point, but I have never given up on the idea I will relocate it to Florida (for winter use) when he's up and gone. My boating these days is more of the go fast variety where I, can drive 55 (Sammy Hagar), and get close to 5MPG doing it. Spending the weekends at anchor and/or riding around at 1MPG or less isn't as appealing when you live on the water and have other boats to play with.
As for the DIY thing, while I do take a certain amount of pride in that (now more for the savings vs the pride), I hardly ever did things I really didn't enjoy doing on a boat (or anything else) when I could pay someone less money than it would cost me in lost earnings time to do myself. If I can earn, let's say $150 per hour at my job, why wouldn't I want to pay someone substantially less than that as to be able to use my free time to actually enjoy using the boat... or whatever. Now that I'm making less than the average mechanic/boat washer charges, I do as much as I can myself. One of those full circle of life things, I suppose.
In the end, there is only so much planning we can do, and fate is the real master. I mean I could drop dead before some of you even get a chance to giggle at this.