Bob's Fleet
Most guys my age have a bag full of golf clubs.  Why so many clubs?  Each club has a specific purpose.  The same goes for skateboards.  There are skateboards built for pools, ditches, downhill, slalom, freestyle, sliding, and street to name a few.  By the time you purchase one of each, you will still have less money in your fleet than most people have in a golf bag.  So drive your wife crazy, get out there and buy some more skateboards. 
Pool Pig Front View    Pool Pig Top View    Pool Pig Bottom View
Pool Pig - Pools, ditches, ramps, parks and all your skateboarding needs.
Deck - Black Label Neil Blender   9.75 x 32
Trucks - Tracker Darts 185mm (I used to have Indies on this board, but Tracker is a much smoother turning truck.  One ride on Tracker and I'll never go back to Independent.)
Wheels - Bones Skate Park Formula 62mm
Bearings - Pleasure Tool Ceramic  (This combination of wheels and bearings is very fast.  Hang on tight.)
Longboard Front View    Longboard Top View    Longboard Bottom View
Longboard - Downhill carving, bombing, giant slalom and cruising around town.
Deck - Land Yachtz Drop Carve   9 x 42 (Flexy)
Trucks - Randall 2 180mm (Stable and turny)
Wheels - Abec 11 70's Flashback 70mm 78a (Great longboard wheels)
Bearings - ABEC 3 el cheapos and they're still too fast for me
Mini Front View    Mini Top View    Mini Bottom View
Mini Board - Slalom, carving, cruising town and skateparks, longboard for the kids, and medicine for your soul.  This is my favorite skateboard.
Deck - GF Hurley 27   7 x 27 (Small, light, and flexy.  Nice camber)
Trucks - GF Hurley 3 Inch Mini Trucks (Khiro bushings - awsome)
Wheels - GF Hurley 70mm 78a (Very fast and grippy)
Bearings - GF Hurley ABEC 5
Slide Board Front View       
Slide Board - Dedicated to sliding and spinning down large steep hills.  The gloves are mandatory.
Deck - Black Label Neil Blender   9.75 x 32 (Same as the Pool Pig)
Trucks - Independent 169 (Used to be on the pig.  Great for sliding)
Wheels - Mini Logo 62mm 99a (They slide very nice)
Bearings - Bones Reds (Cheap, but put up with a lot of abuse)
Street Board Front View    Street Board Top View    Street Board Bottom View
Street Board - Street, freestyle, all forms of kick-flippery
Deck - Mini Logo 8 x 31 (Very mild concave.  Just right for me.)
Trucks - Independent  (I would get Grind King next time.  Lighter weight but still very turny.)
Wheels - Mini Logo 52mm 96a (Good enough for kick flipping.)
Bearings - Bones Reds

The whole fleet

Public Service Announcement - In the mid to late 1990's, very expensive mountain bikes and accessories started hitting the market.  Seeing an opportunity to do some bragging and look cool with a high dollar bike on top of their cars, a lot of yuppies and roadies moved into the scene and turned my beloved sport of mountain biking into a "Keep up with the Jones Fest".
  For me, that ruined the whole spirit and brotherhood of the sport.  Don't let that happen to skateboarding.  Enjoy all the great products and gadgets that modern day skateboarding has to offer, but don't be a jerk about it.  Share your reviews, share some parts, share the stoke.  Skateboards are relatively cheap, there's nothing to brag about.