One of the most difficult flights I've ever done was trying to get the plane back to the dealer for an Annual scheduled before the two year warranty ran out.
Had I missed the deadline by even 1 day, any defects discovered would have not been covered by the warranty. So it was critically important. The autopilot alone was a £20,000 repair job.
It was a low level IFR flight in Class G, in something like OVC006, solid IMC, turbulence, rain, the whole lot.
It had been delayed by about a week due to poor weather every single day, but in the end I decided to go as the weather was technically flyable.
It was uneventful but quite busy, no autopilot.
In the end, the plane sat at the dealer for a couple of weeks before they started on it because all their staff was off to some exhibition or training...
I don't like the "get home itis" concept. People should be trained to make go/no-go decisions based on technical data before them, and continue making the decisions when in the air.
Instead, we have the PPL sausage machine which uses stupid sayings like "better to be on the ground wishing you were in the air than the other way around" to excuse what is a very limited training relative to the privileges. The limited training concept is supported by many people who never want to go anywhere to start with e.g. aerobatic pilots who currently do the same PPL but really they should do a different course entirely.