I have been skateboarding since 10 years old and I am 50 years old. I started on clay wheel and have been through every evolution of skateboards,
I have skated flat,downhill,slalom,Freestyle,street,backyard pools,parks,Even the 22 foot pipes they used to build San Onofre Nuclear power plant you name it I have skated it.
I excelled at raced slalom, freestyle,all around skateboarder as a sponsored amateur and turned pro to get out my Sponsor were Kryptonics wheels, Vans shoes, Cutter trucks and on and off the Tracker truck flow list.
I also owned my own board company called FU skatez of aka: Freestyle underground it was charity board company to sponsor freestyle skateboarders who lost their board sponsors,When the manufactures killed freestyle skateboarding and quit making freestyle boards.. I was also the Head judge and vice president of CASL.
Basically stay away from the cheap board packages from Craig's list and ebay the product is crappy product. You have to figure out how you want to skateboard is it for getting around town, exercise,downhill, pool and park riding,
So you need the right board and trucks and wheels for the form of skateboarding you want to do.
I like to build my own boards some mail order houses will build the boards like you want it.
Trucks by Tracker, Randal are good trucks the other truck companies are just copies of the geometry of these trucks and over priced and hyped to take advantage of the novice.Some are specialized high performance trucks for downhill or slalom for example Seismic trucks use springs and are real stable and wobble free I owned a pair they were fun. Seismic also makes 3DM wheels that are great but expensive.
Plus you can get them in the correct width so your wheels and truck assembly fit under your board so you don't get heel bite when pushing when the trucks are to wide. I use Tracker RTS and RTX slalom 106 mm wide trucks on all my long board to keep the truck and wheel assembly under the board and they turn fast. The widest I would go is 129/130mm trucks on long boards.
Wheels their's alot out their quite a few of them for long boarding and most are manufactured by Chris Chauput's company Abec 11 under different labels. Personally I like the Abec11 Grippins 75A wheels is a great all around wheel that does not chip.
My favorite board in my quiver is the LongBoard Larry walkabout LDP board. I also own quite a few specialized other board in my quiver for each discipline of skateboarding .
If you don't want to spend a lot of money Gravity make great boards,Wheels and owns Randal trucks I like 129 mm Randal trucks. The Burner or Blazer are great wheels in 74a. I like the 35" Burning spear board it's a around shape board, Made out of hard rock maple and jute fiber instead of fiber glass to give it some flex . I like the standard angle risers. Give them a call to get the narrower 129mm Randals trucks when you order.
Long Board Larry's hand makes their custom board in their shop in Oregon,They will help you build your board.
Specialized manufactures for example Never Summer who make their boards like snowboard with P Tex bottom, top and plastic side bumpers and have 3 year guarantee. I like the Norad board. http://neversummer.com/skate/boards/norad
Back a couple of years ago I got hooked on LDP aka: Long Distance Pumping basically of flat ground pumping of the board wiggling like your going through straight slalom cones to generate propulsion with out pushing with your feet. You can cover mega miles and exercise and get around town fast.
You can learn a lot about LDP and long distance skateboarding from Paved wave.
Since you don't have insurance at the very least get some Rollerblade wrist guard that's what use because they are light weight and breath with a plastic hand skid. But I am not a fan of safety equipment and have paid the price once in while. Others wear knee pads and helmets and some also wear elbow pads.
Shoe wise buy Vans or other skateboard shoe on sale.
I have found great Deals at the Vans company stores on their clearance rack or also Ross dress for less. Basically you want a nice flat bottom soled shoe I prefer gum rubber , rubber sole is okay also.
I wish I was still on Vans shoe team I would get 2 pairs a month.
Silverfish is also a great source of all forms of skateboarding.
Hope this helps you out and have fun ,