Fortunately, I've reached the age where I don't need much of an excuse to stay on the ground. I really don't have any remaining bucket list items on my aviation "to-do" list, so repeating a flight I've probably already done in less than enjoyable conditions just doesn't float my boat anymore. I don't require ideal weather, but I'm retired so waiting a day or 2 for comfortable flying conditions isn't a big deal.
Last month it was time for my annual. The weather was marginal at reporting points between my home drome and the private grass field (no METARs) my mechanic operates on. Dense fog dripping to the ground at the half-way point made me turn back twice. Fortunately, weather at my home base staid steady at 1200' ceilings. On my 3rd attempt, I made it all the way to my destination, but wasn't sure I'd be able to land. The strip is short, and uphill to the north, so all landings are to the north and departures are to the south. I had 10 knots of south wind at pattern altitude, but tall trees all around the strip block the wind on the ground. I decided to feel my way in, giving myself permission to abort if I couldn't stabilize the descent through the turbulent layer just above the trees. Fortunately, the descent was steady albeit a bit fast over the ground. I was able to get the plane down with 1/2 of the 1800' strip unused. My annual proceeded as expected and the weather for my flight home was delightful. In the past, I've delayed my annual, or I've flown my plane in and parked it a couple of days in advance to avoid predicted IFR conditions on the day my annual was to start.
turn-back time

Flying from the Seattle area to Maryland in my Maule last summer involved lots of weather detours and several shortened flying days because of persistent afternoon thunderstorms along my route. The same issue plagued me on my return trip. I had to detour from Aberdeen, SD to Salt Lake city because my planed route across the Rockies via Mullen Pass was blocked by thunderstorms, and had been for days. Having extra time available and resources to pay for extra miles can be a life saver! My planned route is in black. The route I actually flew from Aberdeen is in red. This image was put together after I got home, so it doesn't reflect how crappy the weather was where I planned to cross the Rockies.
