Kevin--As I found myself carrying on into greater and greater detail while replying to your PM, I eventually figured I might as well just post it here in case it might be of any utility to anyone else looking to get on board.
I see that in the meantime, Oliver has made some of my points below a little redundant, but rather than going through and tidying it up, I'll leave everything intact. Perhaps it will be of some use to see where our opinions converge and diverge...
*****
Unless there's something specific I'm after that he doesn't carry, I always use
Mile High Skates (link) for my internet orders. Even though he's in Colorado and I'm in Miami, I consider it my "local" store. Mark, the owner (though it isn't his full-time job, just a labor of love operated out of his garage), is a very helpful and knowledgeable guy. He enjoys taking all the time necessary to make sure his customers get exactly what they need, is always very forthcoming with answering questions, and if there's something that he thinks would be a better match for you but he doesn't carry it, he'll tell you so and where to get it--pretty uncommon level of service for a skateshop anymore. I can't recommend him enough, so please feel free to take a look through his site and email him with any questions. Just describe what it is you're looking for the best you can, and he'll be more than happy to guide you through everything else.
The days of the useful local skateshop are long gone--at least for us older guys. You walk in with a pile of money to spend and all the young bucks still give you the stinkeye the minute you walk in the door, and then even after you school them with information, most shops only carry street stuff--boards that have very, very little difference from one to the next in terms of size, shape, durability, wheelbase, dimensions, etc.--the same goes for the trucks and wheels...
I think the easiest way to start figuring out what would be good is whether you think you'd want a kicktail on the board. If so, that narrows the options considerably. If not, then we'll need to figure out some other characteristics you're looking for such as whether it's a top mount (a traditional deck where the trucks bolt to the deck just like you remember) or a drop-through, which is a setup that rides much lower (and is therefore more stable and suitable for higher speeds, but at the expense of curvy carving) because the trucks are mounted through the deck--baseplates on top, inner guts of the truck going through a cutout in the deck, with the hanger below. In case that doesn't make sense,
HERE's a picture... You'll also want to figure out the degree of flex you'd like in the board--a flexier, more limber board will be more responsive to pumping and thrusting (haha) with your weight, sort of like carving hard on skis/snowboard/surfboard but it'll be less stable at speed. A more firm board will remain rigid and keep things locked in and more free of vibration/harmonic resonance/speed wobbles while going quickly.
Personally, I don't care for a very flexy setup. I prefer something that behaves more consistently and predictably, even if I have to give up a little versatility at times. Then again, I don't have a really curvy, carvy, surfy style--I'm more of a straight down the hill kind of guy...
Trucks are pretty much just personal preference on longboards. Randal R-IIs are probably the most commonly used, I've got some of those as well as a set of Crails. Both work just fine, both were pretty easy for me to dial in to my liking, and I honestly don't really give much thought to my trucks after I've got them all set. If you're fussy, pick up an aftermarket bushing kit so that you can get them as precisely tuned as you want.
Wheels are obviously pretty important. I'd recommend just about anything by ABEC-11 other than the Gumballs, which are great wheels if you aren't going too fast or cornering too sharply--they tend to do a sort of "catch and release" sort of unpredictable slide at the worst of times--I've probably left several square feet of skin on the ground due to it... Seismic also makes some great wheels, and while I haven't ridden them personally, a lot of people seem to be going ape (haha) over everything that Orangatang is putting out. Bearings are a crapshoot. I've had cheapos that worked great for a long time and expensive ones that underwhelmed me. Ceramics are worth it if you want to drop the coin, but the cost/benefit ratio is absurd enough that by no means are they necessary. You can't go wrong with Bones bearings.
I'd recommend getting a set of pads and a helmet. I always want to try them on before buying just to make sure they fit right and are comfortable enough, so I've never owned any of the fancier or custom-made brands. Right now I'm using
Triple 8s which I got at a Sports Authority or some such thing. Other older guys swear by
Pain Cheaters,
Pro Design, and
187. Helmets are basically helmets, but make sure to get one. You don't want your family to have to wipe your drool and/or your ass for the next 40 years.
If any of these stores (Barnes & Noble, Borders, Tower, Hastings, Virgin, & Books A Million) have a location near you, give a call or stop by and check to see if they carry
Concrete Wave magazine. It's got a good deal of coverage on longboarding in each issue, as well as plenty of ads that might help inform your decision. They put out an annual buyer's guide with all manner of companies and equipment that you can download
HERE. It isn't the best format to flip through pages, but I suppose it's better than nothing...
Please feel free to ask any questions or advice--I'm happy to help...
Steve