Advice on antennas for portable operation. First suggestion: get rid of the windom. Instead, consider end-fed antenna with a counterpoise wire that is laying on the ground. The end-fed antenna can be different lengths but I have been successful with 40 to about 60 feet depending on the band I am operating.
My procedure is to use a nearby tree -- hopefully there is a nearby tree, if not there are some other solutions. Get yourself a sling-shot and some fishing line and a fishing lead weight (not too heavy). Run out about 50 to 75 feet of fishing line, laying on the ground in a way that it will not get tangled when you launch one end of the line up into a tree or over a tree using the sling shot and lead weight. Practice doing this at home -- I am pretty good, normally takes one shot, rarely more than two.
Using the fishing line, now attached at one end to your antenna wire, haul up the antenna wire to a good height. Branches are usually not a problem with most trees as the wire just sits on top of them. Attach the antenna wire at your transceiver to the adapter using a convenient method. I modified a PL-259 to connect the antenna wire to the center pin and a ground counterpoise wire to the ground side of the PL-259. The counterpoise merely lays on the ground stretched out in a direction that works best for the direction you want. Experiment. I use a length of counterpoise wire of about 28 to 30 feet and sometimes more. I have lots of little homemade spools of counterpoise wire of varying lengths.
If you have no trees available, you can do something I did a few times although it costs a little. A telescoping fiberglass pole. I usually had my pickup truck with me and I could put the bottom of the telescoping pole in the stake hole in the back. I have used such a pole for center fed 20-meter V-dipole and for end-Fed antennas. Unfortunately, I broke the fiberglass pole and never replaced it.
I bought a Buddipole Delux antenna with an additional 18 foot telescoping pole that I use most of the time now. I use Dacron lines to guy the extended 18 foot pole though most of the time I do not go all the way to 18 feet, usually about 15 feet but it is sitting in a tripod which lifts it off the ground about 2 feet. The Buddipole works great and I have the most contacts on that antenna -- usually near the ocean on the Oregon coast or Washington coast.
All my QSOs are CW QRP with a variety of transceivers (Norcal 40A on 40-meters, Elecraft KX1, Elecraft KX3 and KX2 on 40/20/17/15. I always use an antenna tuner but with the Buddipole I can usually get a good match at under 2:1 SWR, in fact on 20 usually 1.5:1. I just recently sold the KX2 so my next portable ops will be with the KX3.
I typically use antennas that are easy and fast to setup and take down. After arriving at a site, I am usually operating with the Buddipole in 30 minutes or less.