Some ideas for you,
I'm at the opposite end of the spectrum (just enough hours IMHO at c 25-30 per year). Philosophy, however is the same as IO540. Do different, interesting, slightly challenging stuff.
Best way I have found is to to plan rather than decide on a whim. I have kept to it over the past 2 years.
Skills:
Last year - IMC (yes I know you're past that)
This year - Taildragger course on a SuperCub
Hopefully this summer - Moths
Next year - possibly basic aeros
Places:
Try to fly on hols and when working abroad (US and Portugal last year).
Can't justify my own a/c yet, but still manage fewer, but longer half day or day long trips:
Last year - L2K with family - meal, beach - great
This year - Duxford and it's museums - a challenge in IMC as I found out.
Hopefully this summer - IOW
Next year - a Channel Island - possibly Guernsey or Jersey
Within next five years:
- buy into a Jodel group or similar
- French vineyards
- visit Ma in Alicante
- complex rating (only if I'm earning bigger bucks)
- mountain flying course
- Alps? New Zealand?
And when the weather is just right. Go VFR on top and skim those cumulus...
Enjoy