So all this talk about winches got me thinking " I haven't run my winch since Spring". Now this either means I have been fortunate or I have not pushed things hard enough. Likely a bit of both.
I have never lubricated the cable so I thought this would be a good idea as Kevin suggested. I went out and picked up the chain/cable lube at the local Napa and was ready to spool out. Hooked up the controller, pushed the toggle to spool out, only to hear "click, click"

. Cable moved 1/2" and that was it. Looks like a solenoid problem in the winch.
Ok so the winch is out of commission. I then decide to go to out with the truck to the CDN Tire since it is out and warmed up. Drive on the highway and come down the off-ramp and the truck dies. Pull over and restart and drive 100m - truck dies again. After that it restarted and I made it home with fingers crossed. Truck is currently getting the components in the winch replaced and/or rebuilt and a remote PMD installed (and a spare replacement in the glovebox should there be a future failure). Figure I was lucky being that was close to home.
Conclusions / lessons learned / notes to self:
1. Count these setbacks as blessings. All this is better to happen now in the offseason as opposed to on the trail in the middle of nowhere in July.
2. Don't assume that because something work last time when you were finished with it that it will work the next time.
3. The Hummer remains true to form at about $1000/ month average in maintenance, service and new accessories.
4. If in doubt or if has been awhile - replace it. I was living on borrowed time as I believe the PMD that failed was original to my 1998 H1. The guts on my Warn winch are original as well so 17 years later how reliable could I expect it to be?
Thanks Kevin - the lessons above started with the "lubricate your winch steel cable" suggestion. Likely saved me from a lot more time, frustration and disappointment on the next offroad.