Since our OB population averages around 250 lbs (and regularly gets near 400), I've got some experience with this population.
1) Discussion of risks and benefits and that the risks of pretty much everything (difficult placement, WT, predominantly) are higher because of their size.
2) Finding midline is my key and can be hard to do without palpable landmarks. I do the following:
a) Between about 175 and 300 pounds, the lovehandles and the spine make a nice cross right at about T11-L1 roughly. This is usually a great place to start.
b) above 300 lbs, though, for whatever reason, the physical and architectural integrity of their largesse breaks down, so you sort of just have to eyeball it.
c) I really try to find spinous process and map it out with my local needle. If I can't reach it with my local needle, I'll use a 20g or 18g spinal needle just to find the process to approximate midline. I know people say that spinous processes can be off kilter and be really misleading, but I think that's pretty rare. All I can say for sure is that if I have a good, reliable contact with the spinous process by one of these methods, I have a really high success rate hitting ligamentum flavum and, ultimately, getting a good epidural.
3) beyond that, it's a matter of keeping the catheter in. In the gorillas, there's a lot of "skin" between the surface and where that catheter is anchored by LF and lots of movement by the patient can supposedly really torque on it. I can't think of the last time I had a laboring patient work their catheter out, though.
4) we have a decent number of patients who ultimately require more than the 10 cm Hustead needle, so we stock what I believe are 15 or 17cm needles, and the accompanying longer spinal needles for CSE. It's really something to watch the babydaddy's eyes widen when they see us whip that badboy out.
Anyway, that's what I do, and it seems to work a high percentage of the time.
As for the bloodpatches, I almost never do them. I've had 4 or 5 wet taps in the last 2 years and left the catheter in the intrathecal space in 4 of them for 24 hrs and none developed headaches.