That definitely looks like a good candidate for a cleanup. Looking closer at your pics shows there's been some good work to update the water system, various hoses, and moving some equipment to a more maintenance friendly locations.
The one piece of advice I'd offer to anyone going down this path is to carefully plan everything out to ensure you have most everything you need on hand and the environment is good to paint (temp and humidity). The strut replacement project has really masked a lot of my mistakes in planning this out. At first I was just going to paint and install insulation, but I added the hoses, then thru hulls, then..... If I just would have looked at everything before hand and went for it, I would have saved weeks of time. In my case, it didn't affect the timeline because the strut work is still going on (fingers crossed they will finish up the fiberglass and fairing work this week).
It is actually a very doable DIY project. Removing the engine was surprisingly easy and each individual step was straight forward. You just have to put a plan together and go through each step. I'm not done yet, but I would say it's been worth it and I'm actually looking forward to maintaining the engine after this work is done. Before, I would put off the routine maintenance until the last possible minute. There's been many trips over the last few years where I was at the boat late the night before struggling through an oil change, fuel filter replacement, or stuffing box adjustment. Hopefully this will make all those tasks much more tolerable.