Felt the same way 2-3 years ago until I discovered Rockbox. Then my Classic was reborn and I still use it every single day.
The Emcore versions I'd recommend are r859 and r862. As for the version of Rockbox, I use new daily builds.
In Emcore you can set to auto boot Rockbox, that saves a bit of time. I'm not sure, but you might be able to make it a bit faster by manually removing the games and apps from the .rockbox-folder. The original firmware has this hibernate function, compared to that Rockbox boots somewhat slowly on the Classic. I've set my Classic to auto resume playback upon booting, from fully switched off to hearing music takes 9 seconds.
And remember, Rockbox is firmware/software. It gives you complete freedom to adjust the device according to your preferences, but it doesn't magically increase the quality of the headphone jack :-)
Edit: 200 pages and almost 3000 posts; this thread got big" src="http://files.head-fi.org/images/smilies/biggrin.gif">
Do you have a link where I can download emcore r862?