Jerry...I promise you that nobody would ride with the Legends slammed more than 100 feet if the road wasn't perfectly smooth...it's worse than riding a hardtail. The stops will literally bounce you off the seat...

I always try and remember to pump them up just a little after my BSR gets on the bike, but I have forgotten a couple of times...as soon as I go over the dip from my driveway to the street, at less than 5mph, I get reminded in no uncertain terms.

One concern with those kinds of shocks is what happens if something leaks, the compressor goes out, the solenoid fails open (not likely), switch goes bad, etc. For that reason, I have mine plumbed up to the original schraeder valve behind the left saddlebag, and I keep a little tubing down in the saddlebag...I can always bypass the problem and air them up at a gas station enough to get home. Of course, if the shock itself takes a crap (unlikely since they have Kevlar boots), you're hosed, but you would be with any shock that totally failed. With a 29" inseam, I can still get my feet on the ground pretty well fully aired up, but I'm just more comfortable with them down a bit for parking, loading and unloading the BSR, etc.
Good boots make a huge difference with a bike as heavy as ours, and your advice of boots and modding the seat a bit is sound. I just knew already that it wouldn't be an effective solution for my needs/wants. As you mentioned, I would never drop a Harley touring platform more than an inch.