Buck, stop messing with the poor guy
Better tone means better tone. You'll get it one day, just keep playing. For now, you might experiment with various brands of strings until you find one that you like. You'll know you like em because you'll like em, simple as that really!
I play Ernie Ball Power Slinkies (.11-.48) and would recommend anything in the slinky line. Since you seem relatively new to the guitar, I'd recommend either Regular Slinky or Slinky Hybrids. The regulars are 10's and the hybrids are a mix between regulars and power slinkies (fatter on top, lighter on bottom). Don't play with lightweight strings too long, you'll just be doing yourself a major disservice, no matter how difficult heavier strings feel at first.
As far as changing your strings... You should feel when they start getting nasty. They'll feel ugly and they'll sound even uglier. Hell, they'll even LOOK ugly. If I let it go for a long time, I'll probably change the strings on my acoustics once every couple of months. With heavy playing, however, it'll be as often as once per month. Now that's not because they don't need changing more frequently, it's simply because I'm lazy.
Now the electric is a different story. I'll probably change the strings on my les paul at least once a month, or at most every two weeks. Well that's not true, if I'm playing hard I'll break as many as one or two strings, meaning a string change every other day or so. But that's not normal "home studio" playing.
One product that you absolutely NEED in your case is a bottle of magic substance called "Guitar Honey". I'm not sure what the shit is, but I'm pretty sure it's magical. What you need to do is remove the old strings from you guitar, then with a damp cloth wipe all the nasty gunk off the fretboard. Make sure the fretboard is dry, then spray on a squirt of guitar honey between each fret (don't worry if it runs off). Once it's soaked, let it sit for about 30 seconds, then take a clean cloth and really rub hard between each fret until the board soaks up all of the magical substance. If the board feels completely dry to the touch after this, then apply another coat of guitar honey in the same fashion as the first. At this point, the fretboard shouldn't feel wet, but it should feel cool and a little bit oily. Now put fresh strings on your guitar. I guarantee that if you followed all these steps, you will literally have no choice but to take off your pants and have sex with your guitar...it'll feel THAT good.
And since you're changing your strings now, you might as well learn how to adjust your intonation. Despite what some people say, you can get it close enough with a regular guitar tuner and a small screwdriver. Do some searching.
Finally, if you've never had it done, or you change string weights, you'll want to take your guitar in and have it setup. They will adjust the neck, intonation, and action for you. The key here is to WATCH them do it. Once you kind of get a feel for things, you can make the adjustments yourself. The only thing I don't personally do myself is adjust the truss rod, because it can make this really nasty creeky noise that scares the crap out of me.
Just remember, most of your tone comes directly from the guitar which is just an extention of YOU. Amplifiers play a big role, but only if you know what you're doing in the first place. Same with effects, which are a new player's worst enemy.
Slackmaster 2000