Ok, first of all let me put my own disclaimer out there.
1. I am a newbie - in regards to Linux/xterminal/packaging/debs/etc I dont know my *** from my elbow.
2. Which brings me to point no. 2, please refrain from telling me what I can not do. I am willing to learn as long as it doesn't require a background in IT engineering or a degree in computer science. If you think the process is too difficult for a beginner, be polite. there's no need to be condescending for even the greatest at one point knew nothing.
Having said that, I've been thinking about installing an alternative OS on the device so that I can run more desktop-like programs on there. proxies, IM programs, etc. I know there are threads out there discussing the other available OS's but my question is...is it worth it? which OS is the easiest/most stable to install and use....
and how difficult is it to learn for someone who doesn't know know how to use Linux or "crack" into Maemo? how do I start?
Booting an alternative OS? I wouldn't recommend. Primarily because of your point #1 and the extreme difficulty and the processes involved.
However... Everything you listed in your second paragraph should be possible with Easy Debian... and that I would recommend if you're willing to learn and test a bit.
I second what fatalsaint says. If you are looking for a regular desktop and more desktoppy applications, easy debian is the way to go. The other OSes aren't really usable yet.
I agree with these two. The OS is solid and hackable as is, and with your background, the last thing you're gonna need is a huge unknown quantity. Start small with something that interests you; you mentioned proxies. Setup scratchbox and build tsocks. After you get that up and running, come back and see us, but forget about different OS's for the time being, except for maybe an Easy Debian or Easy Mer chroot.
Sorry, that's about as uncondescending as I can be.
