I used to do many of these things myself earlier and even enjoyed it a lot; I did the mowing, the tree planting and trimming, and most interior things including finishing everything in a 2000 square foot sun room and walk out basement, including electric, extensive tile work, a cedar sauna, and a large bar and game room which has a lot of stained oak paneling on the walls. But looking back, to some extent it was a matter of proving to myself that I can do it, and now I have other interests that I want to use my time for.
So my view has evolved, and now for me the answer has two parts. Currently they are a matter of choice, but they would similarly apply to the time down the road when I just couldn't do these things anymore.
First, have a really good handyman. After literally years of trying, I have succeeded at both the place up north and the one in Florida, one of them has been with me for twelve years, and the other for three years. The quality of the handyman matters a lot, I have tried many others before, but after a while you get a sense of their quality and you know a good handyman when you see him. One of them charges about $20/hour, but he is so reliable I don't even measure his time or get an estimate ahead of time, he just bills after the fact and is very fair. The other charges $30/hour, which is a bit on the higher end, but he is super efficient, very conscientious, and also very fair. I make sure to show them that I appreciate their work, by giving them little extras, donate some of my tools I don't need anymore, give them a pie when I bake, and give presents for kids birthdays and Christmas etc. Just being a nice human being, good folks will recognize it and return the favor in form of quality work, and those that don't recognize it are usually not worth keeping.
Second, strategically hire out most of the recurring services. The first was snow plowing up north. I have had the same guy for more than 25 years, and since that time he hasn't raised his price once. He still does my 600 foot long driveway including a circle in front of the house for $20, and often in the middle of the night if a storm is coming through. No way I would do that myself. Next came mowing. I used to do that with a lawn tractor, but it took me more than three hours including trimming, and there is just so much maintenance on a lawn tractor and even the gas just adds up. Now I have a company that does it for $100 a pop. Sure it's serious money, but I just don't want to work for such a long time and then risk getting teased by the daughters for having a "farmer's tan" yet again
Down south all the landscaping, trimming, irrigation is taken care of by the HOA, and (if you speak enough Spanish) you can even get them to do it the way you like. So that place is also lock up ready and I can leave at any time I please. But I still use the handyman for the interior things: the place has very high ceilings and I just don't feel like monkeying around on a tall ladder, and I think I have done my life's share of interior painting and all the other similar stuff as well.