Yo, so I just started playing Oblivion on the playstation 3, and I killed an imperial guard that was walking around because I thought he was just some random dude, but I thought it was no big deal and I got an outfit out of it. I was heading to a town to join the mage's guild, but the guard to the town got super angry so I had to kill him too. Then later I went to an inn and what do you know, there was a guard there too. Now my bounty is like 3500 and I've read all the ways to get rid of it, but I'm not sure what I want to do. What I'm thinking of doing is stuffing all my stolen junk in a chest, saving, and going to jail and resetting it until my sneak and security skills go up rather than my other skills going down. What do you guys think? Will that work?

You seem partial to stealing considering you mention you have a bunch of stolen junk. Why not join the thieve's guild and pay off your bounty that way?

Hmm can I join the thieve's guild without going into a city? If so, it sounds like a good idea. And I don't have a lot of stolen stuff, I'm sorry, I just meant the outfit lol.

Pretty sure the outfit isn't stolen. Pickpocketing and taking things from homes and stores are stealing, but I think you can take what you want from people you murder.

Good to know, thanks man.

I don't think your security or sneak skills can actualy go up from going to prison. Not directly anyway. When they say that what I think they mean is that you can increase them by using them to escape prison. When you get arrested you can manage to keep one of you lockpicks which you can then use to unlock you cell door then proceed to sneak out. You need to be good at lock picking or have a really high security level to be able to do it though. It may also be easier to fight your way out than to sneak. Either way your bounty will increase for escaping. Personaly I think the best way to go would be to join the thieves guild but as you said it will be hard to do if every guard you walk past attacks you. I think you may have to just accept the prison sentence if you can't pay off the bounty. I never thought the stats penalties for doing so were really all that much. If you ever do atempt to escape from prison, don't forget to grab all of your confiscated stuff before you leave. It's usualy in a chest somewhere outside of the cellblock area.

Actually, every night you spend in jail (1 night per 100 septim bounty) a skill is chosen at random. If the skill is security or sneak it will go up by one point. If it is any other skill it will go down by a point. No skill will be decreased by more than 10 points on any single incarceration.

Yeah, that's what I ended up doing. My only major skill that went down was armorer by 2 points, no big deal. Thanks for the replies guys!