Yesterday, I went to cycle the top for the first time this season as it was decent weather in upstate NY and I unlatched the header, windows rolled down, push the button and I could hear the system working(or trying to) but the rear deck wouldn't lift. Any suggestions?

 

Sounds to me like low fluid. You may have to open it manually and check for low fluid and leaks.

 

If the pump was running and nothing was moving, you have low fluid and that means a leak. This will be expensive, but it is fixable. Klaus / Top Hydralics is your friend, he's on here and will probably see your post.

I very much believe in exercising the top system OFTEN. My last car died at 116,000 miles and was a daily driver. I put the top up and down several times a week - and more often in summer, sometimes 4 times a DAY - never had an issue.

Seems like those who store their cars have the most trouble - I think top systems are like human bodies, sedentary lifestyles cause harm!