What am I getting myself in to?

Welcome Joe!  

I haven't looked at the package deals.  In general, if the package is all or most of what you'd buy separately, it may be worth getting the package, but if you'd pick different things, the package isn't such a great buy since you'll end up with not what you want.  Also, the kit may include things you don't really need.  As an example, what HIM are you targeting?  The kit might include a wetsuit that you either don't need or cannot use in your race.  

It's easy to get wrapped up in gear, but the reality is once you've got a basic setup, buying newer or more expensive gear will produce only marginal gains.  

Key to success is to train consistently.  Find a plan or hire a coach and follow the training plan.  If you use a canned plan (BT has some decent ones), understand that these plans don't account for your specific circumstances (fitness as well as other life) so don't be a slave to the plan.  If you're hiring a coach, your training week-by-week should be specific to you and you'll want to execute as planned.  If you're having a problem, talk with your coach.