I am re-equiping myself slowly but steadily with second hand gear. Last year I bought off flea bay a rig, a 6.7 RX2 Neil Pryde sail with complentary NP carbon boom and mast.
I really love the combo. Even though the stuff is about 7 years old I have found it fast, stable and comfortable.
I bought another older NP race sail off eBay, A 5.9 VX2 I think. It looks good for its age and I look forward to stronger winds to use it with. Back in the day when I was good at windsurfing, these were the bees knees but I could never afford one. Fast as greesed lightning.
I just purchased off Seabreeze buy and sell another NP race sail, this time a 7.2 RS6. The design is really amazing, the wide luff seems to be like a wing mast. Its very different to the RX
Anyway its a bit scary with this new sail but I look forward to trying it out. All up my NP quiver cost me around $900. I'd rather buy second hand top spec race gear than newer detuned designs.
How do you feel when you get new (to you) gear thats going to challenge you?
I recently bought a new board (my old 84l Starboard Trance developed a huge bubble in the front of the hull and sounded and felt like I was pushing a drum through the water in front of me) - so I bought a new 79l Starboard Kombat.
The main thing I noticed was how my own sailing changed, I was pushing to see what the new board could do and so pushing myself a bit harder and (to my mind at least) sailing better.
I think when you have the same gear for a long time (4 years for the trance) you tend to get into a rut and not try new things or push the limits as much.
For me anyway new sails dont seem to have as much effect, although I do now know what spot1 kept telling me about how good a skinny mast feels during a gybe, the kombat keeps planing through the gybe where the trance tended to slow down a lot.
Yep its always good to try a different board or sail, I tend to get a bit dispondent with the new gear claims that always say this years version is soooo much better than last years. OK so there's R&D etc but really how much of it is just a nip and tuck here or there with a rehash of something previously done eg wide boards - narrow then wide etc, sails fuller - flatter twistier. Maybe your right moby, just get 5 year old stuff as it comes back into fashion ( but somehow much much faster).
Maybe I'm just getting old and cynical
The only other thing this brings to mind is how nice it is to get a new sail and be able to SEE through it. I usually only replace my sails when they are worn out, so the last few seasons of use I'm sailing / gybing blind on the downwind side - and thats my excuse for anyone I nearly collide with.
But doesn't brand new gear smell nice 
Don't care if it's windsurfing gear or electronics or cars, there's something about half-cured plastic that just makes me go AAAaaaaaahhhhhh 
Yes... I was amazed at how much heavier the water traffic got when I bought a new sail.
I've no idea where they all came from.
My girlfriend thinks i'm very very strange when i open a new electrical goods box and stick my head in.
"Do you get intimidated by new gear?"
New gear doesn't intimidate me but more so the..............price$$$$$$$
