SoCal Spartan,
I believe that target date funds are great, so that you never have to worry about your retirement funds, just set auto contributions and forget. Gives you freedom to focus on your other investments to make FI. Some people don't like them since it's less customization, or gets too conservative too fast. However, I feel you can customize your taxed/early retirement funds. Also, just mess with the target date in order to choose when to get conservative, as was already suggested.
So for rolling over your 401k, I'm actually in the process of doing that now. Take advantage of Vanguard's concierge service. They'll make sure that everything is being set up correctly, and even conference call the other institution (fidelity in your case). Very nice service. As for what to roll over to, I am with you. Since the money is not much, and I can afford the taxes on $2,500, I'd rather roll it over to a roth and pay the taxes now, than pay the taxes that that amount would become upon retirement. You'll get a lot of arguments, as people will say "but your tax rate will be lower in retirement." Well there's no guarantee if you have a lot of investments and are just raking in the passive income by that point. So if you can afford the taxes now, that's what I would do/am doing. Not saying the other side doesn't bring up good points too, so I think in the end it's personal preference: taxes on 2,500 now, or taxes on 250,000 much later. At our age, I choose now.
Vanguard informed me that the best way to do the conversion, is to roll it over to a traditional IRA first, and then do a roth conversion. Apparently (and you'll see this to be true when working on the transfer paperwork) it's an easier paper trail for the feds to follow, and therefore less chances of being audited and so forth.
Hope this helps get you closer!