I have an iPad2 and I've been very happy with it. As far as timing goes...yeah, it's a tough call whether to buy one or not - easy answer would be to hold off until Spring but with the new BF discounts, maybe it's worth going for it.
I'd use it for a few months until iPad3 comes out then sell off the iPad2 via Instant Sale, eBay or Craigslist for a decent price. You won't come out even but if you only lost...say for example, $100 and the iPad3 comes out in...like April. $100 for 5 months doesn't sound too bad
I sold my iPad1 when iPad2 came out, and I think I ended up paying just around $150 difference.