RE: A perfect day, every day..
It's tough to have a perfect day every day, but I've found some good ways to do it.
1. Always bring a longboard or a hybrid. Sailing them can be a nice, relaxing experience. You won't ever feel like you wasted the day, even if you don't plane.
2. Sail with a friend, teach a beginner, or participate in a longboard race. With someone to interact with on the beach and on the water, you won't care if you aren't planing. If you get into racing longboards or hybrids, you can always "practice" even if you're by alone.
3. Stick close to home. With gear that can make the most of light or gusty winds, you can have fun without driving so far. That takes some of the pressure off, i.e. you don't feel like you HAVE to plane to make it worth the trip. And you can have a session in a shorter amount of time, i.e. after work.
4. Do some exploring. (This seems to contradict #3, but it really doesn't). With longboards and hybrids you can explore upwind and downwind along coastlines or inland waterways, and maybe find a quiet beach to go for a picnic or something.
5. Some basic freestyle is pretty fun. I don't do anything fancy, but it's fun to sail backwinded and do weird tacks and stuff.