If you're as handy as you say, you should have no trouble with the work, by all means go ahead.
I have a nice concrete floor in the garage, and I use ramps. Those are good, but of course there are several possible arrangements. For safety I recommend only ramps or jack stands. Getting under a car with jacks alone are an invitation to a funeral.
That being said, with regular (Rhino Ramp) ramps, I had no trouble accessing the belly pan and the drain for the DSG, and I am big (6'6", 285).
The materials to do the service are easily acquired from a dealer, but you'll almost certainly pay more. I got them at the local dealer, but I used the VW Dealer Goodwill VISA to do it, which has to be spent there. Probably the best place to get the DSG oil and filter is from idparts, and they are supporting vendors of this forum. Their price is good, and in my experience their shipping is prompt.
As far as tools, it turned out I had some, and not others. You will need:
10mm wrench to remove battery terminals
13mm socket wrench to remove battery clamp
12mm socket wrench (??) to remove three bolts holding down battery tray, two under the battery itself, and one holding down the "ear" of the battery tray at the right front
6mm hex wrench to loosen bolt holding air box down onto battery tray. (Note: this bolt cannot be taken out completely, just unscrew until it's not engaging the battery tray underneath. Once this bolt is loose, and the three 12mm bolts above are taken out, the air box can be "popped" off the battery tray, and mine did take a pretty good pull to pop it loose.)
The battery tray is an odd shape, and I just worked it around until it came out. The video in the link I put in the OP is invaluable in learning these moves; I watched it several times.
Once the battery tray is out, this exposes the DSG filter housing. You'll need a 24mm (or 15/16") socket to remove the cap, and be sure you have about a foot of extensions for your socket wrench. Some videos show guys using huge deep sockets to do this, but that's not needed. I bought a 24mm socket off Amazon that's nice and shallow, made specifically to do jobs like this.
Something handy may be a pick of some kind to pull the old "O" ring off the cap.
I used the Hoppy "Flo-Tool" to fill the DSG with new oil. This thing is cheap and available on Amazon or Wal-Mart, probably lots of other places. The nozzle that comes on the end of its hose fits exactly in the opening in the DSG housing. As I mentioned in the OP, you'll be doing yourself a favor if you heat up those bottles of new oil. I just used hot tap water in the kitchen sink, made the oil go in about 5 min. / liter. I just hung the "Flo-Tool" on a wire from a hole in the hood, and would refill it when it got low.
Underneath, you are going to have to take out a bunch of fasteners to get the belly pan off. There are four T25 fasteners down each side and one in the front center, total = 9 X T25s. There are 3 x T40s across the back of the belly pan— these were harder to get out than the smaller Torx fasteners, I had to put the Torx adapter in a 1/4" socket to get enough leverage.
The biggest issue I encountered in removing the belly pan was not the fasteners, it was in pushing loose two plastic "teeth" that come down through holes in the belly pan, which an inspection will reveal. You must push these UP before you can slide off the fingers holding the belly pan to the underside of the bumper.
Once the *&^%^&#& belly pan is off, the rest is clear sailing. You will need a 14mm hex adapter (the one in my set was for 1/2" socket set) to remove the big main drain plug. You may want to pick up a new washer for the drain plug, although the old one on mine was not compressed in the slightest. I had no trouble breaking loose the plug, which makes me highly suspicious that the factory didn't torque that thing down to any 25nm. I never torque drain bolts in any case, just snug them down and give one good pull...and in 50 years, I've never had a drain plug back out on me.
Once the initial drain of oil is out of the DSG, you'll need an 8mm hex adapter. The one that came with the set I bought was for a 3/8" socket set. Once the snorkel is out (it's about 6" long) the rest of the oil (most of it) will drain. My car was serviced warm, so it didn't take long to drain completely.
One more caveat, although you've probably already read it somewhere else: don't attempt to wrench that snorkel back in place. When you screw it back up there, just make it finger tight, and forget about it. It's not going anyplace, and that way there's no risk of damaging it.