I was in a very similar situation a few years back and decided to go electric. I knew that acoustic was a better learning platform, but I rationalized that the extra fun in playing around with amplification and sounds would help me retain interest in playing...I'd say it has definitely helped.
Electric action is much lighter, so it's "easier" to play. Going from acoustic to electric, the electric action feels like greased lightning. Going the other direction can be a bit of a rude awakening...nothing terrible, but you do build better hand/finger strength on an acoustic.
I'd say the decision ultimately depends on your goals with the instrument. If you're looking to really learn to play guitar the "right way", I think most would say acoustic first. If you're just looking for something fun to play around with, with no "serious" aspirations (which describes me), go electric...it's probably more fun out-of-the-box. At least that's what it's been for me.
My first electric is here:http://www.godinguitars.com/godinfreewayclassicp.htm
I highly recommend this guitar to any beginner looking to get into a quality electric on the cheap. You will be hard-pressed to find a negative review on this guitar anywhere...I'd venture to say that it's the best guitar you can find at that price point. Yes, it's a little outside your price range, but not by much. You should be able to find one around $400-ish...less if you can find one used.
My first amp is here:http://www.behringer.com/GM110/index.cfm?lang=eng
Again, hard-pressed to find a negative review on this amp anywhere. You should be able to find one around $100-ish...less if you really try. Check out some of the reviews here:http://reviews.harmony-central.com/r...110+Combo/10/1
Altogether, you should be able to get both the amp & guitar for $500-ish new. I think it's a tough combo to beat at the price point...truly.
Lastly, you can forego an amp altogether by patching directly into your PC and playing back through your speakers. I use an M-Audio DMP3 preamp between my guitar and my EMU 1212 to do just this with decent results. The EMU software bundle comes with a bunch of cool sounds...it's fun to play around with.
Hope it helps.
Edited to include obligatory, self-serving pic: