1.  My finger tips are hurting way more than I ever remember them hurting when I started playing back in the day.  Is there any kind of quick fix for this, like using a particular guage string?  I think I've got light guage strings on now.

2.  If my hands are clean when I begin playing and I play for an hour per day, roughly how long can I expect my strings to last?

3.  When I put new strings on, they seem to have a really difficult time staying in tune.  I seem to remember stretching them while stringing the guitar but I can't really remember the specifics.  Should I be doing something something special other than just putting those suckers on and tuning them up?

Any help will be greatly appreciated.  Thanks in advance!

You could try a lighter set to start, but even a guy like me who has been playing pretty consistently (consistently badly that is) still gets finger tip soreness from time to time. Unless it is unbearable, I'd try to stick it out.  It doesn't sound like you've got anything terribly heavy on there.

2.  If my hands are clean when I begin playing and I play for an hour per day, roughly how long can I expect my strings to last?

This changes from player to player, and all depends on how acidic yor sweat is and other scientific stuff like that. If you keep your hands and clean AND wipe down the strings afterwards with a clean cloth you should be able to get several weeks, maybe even months, out of a new set of strings.

3.  When I put new strings on, they seem to have a really difficult time staying in tune.  I seem to remember stretching them while stringing the guitar but I can't really remember the specifics.  Should I be doing something something special other than just putting those suckers on and tuning them up?

Yeah, new strings have to stretch out a bit.  Here's what I do:

- Change the strings one at a time. When the new string is on, tune up to pitch (or as close as you can get it).

- Fret the string at the first fret. Take your picking hand and start tugging gently on the string, just to the point where you can feel it start to stretch.

- Start right behind the first fret and gradually move up the neck to the bridge, stretching gently all the way..the point being that you don't want to stretch out just one portion of the string, but as much of the length as possible.

- Tune the string back up to pitch, and repeat...but even gentler the second time around. Two or three passes should get you pretty close.

- With plain strings, I like to use a pick instead of my fingers to graps the string and stretch it. Plain strings will stretch out a lot easier and quicker than wound strings will, typically.

- Once you've done all the strings, tune the guitar up and let it sit for a couple of hours to let the strings settle in a bit.

My own experience is that when you stretch strings, you should really not try to stretch the string out all the way, just get it somewhat close and let them break in on their own (which really doesn't take that long).  If you're changing the strings right before a show, you'll probably need to be a bit more aggressive.