Yes, No, Maybe.....
I think I am the same as most other folks here. Normal routine stuff I will do such as oil, fuel filter, water pump impeller changes, rebed stuff, painting, rewire, etc. But....
1) anything that requires skill/experience or if done wrong will add negative value to the boat, or
2) requires special tools or several hands to accomplish, or
3) Fuel tank cleaning, hull scraping, etc. (Mike Rowe type of jobs)
I won't do.
The goal is to optimize sailing time versus fix time. If paying someone will get me more sailing time and is not too costly, I will consider it.