I'd go with the bundle, as it will save you more in the long run, though I don't have any numbers to support that. It's also nice only having one bill.
As far as packages go, they are all good deals, but it depends on what you want. If you're content with just a basic package, than that's the best deal for you. If you don't mind dropping 130 bucks/month, then all 300 channels is a good deal, relatively speaking. On top of whatever you get, I like the "sports" package, which gives you a ton of channels (mostly regional fox sports nets) for 12/month or so (depending on what else you have).
I would HIGHLY recommend a DVR. In fact, if you can get a DVR for every TV in your house, that's even better. It costs the same per month (6 bucks I think) to have one DVR and 9 other receivers or 10 DVRs, so you're best bet is to get all DVRs. You can upgrade later to an HD DVR, or regular receiver. It will cost you an extra 10/month to add HD to your package, but that will cover all of your receivers (i.e. if you swap 2 or 3 more standard receivers elsewhere in the house for HD DVRs, it won't cost any extra in terms of monthly fees). You can use an HD receiver with a SD television (generally speaking), so if they are offering up free HD hardware, take them up on it.