I use a trimmer that's made for sideburns and whatnot. Works well. I find that the cut edge of those hairs doesn't bother me at all. Like you, if I shave, it's absolute agony when growing back in. Itchy beyond belief!
For lube, I go with Slippery Stuff. There's a big bottle they make, it comes with a pump top. It feels a little ridiculous at first, sure, but the pump top saves time and is easier to manage in the ... heat of the moment than any kind of cap. I buy locally from a sex shop on the university campus I work on, because they sell at cost. Big bottle runs around sixteen bucks. I would try eBay. I've had good luck with buying sexy things on eBay. Cheap and discrete.
Actually, if you have any sex shops around, you may want to go try some lubes. It's difficult to tell what something will be like in the store, but they'll often have single use sample packs that you can buy. Find out what you like. Then go find it cheaper somewhere else!