Jon, First, if you don't like the frigid winters up there in San Angelo, try moving down to some civilized part of the world... like the Hill Country! Second, are the bluebonnets out yet around that man made lake you have up there? I rode around that lake a few years ago and was shocked at how great the bluebonnets were.
To your starting problem... first, this type problem needs to be tackled systematically. Here is the way the system works that you are messing with...
Power goes to ignition switch and once key is turned on flows through the switch to the starter button. When the button is depressed, it flows through the button to the starter solenoid. Power flows TO the solenoid directly from the battery. The starter is directly connected to the solenoid. The power from the button comes in and TRIGGERS the solenoid which is essentially a relay and the solenoid closes and allows power to pass through the solenoid and go to the starter.
To check this system, I find it useful to do this:
1. check starter function. Make sure battery has good charge. Use a SLOW voltage trickle charger... The charger should have real small aligator clips and be rated to charge in about 12 hours at 1 amp. Once the charge is good, get a piece of 12 gauge wire. Leave the key off as you don't want to power the coils. Take the wire and touch one end on the PLUS terminal of the battery. Look at your solenoid. note there is already a wire coming from the PLUS terminal and connected to the solenoid. There is ANOTHER lug on the solenoid where a cable is connected. This is the wire to the starter. Take your 12 ga. wire, holding the one end on the PLUS terminal of the battery and the other on the the starter cable lug on the battery. The bike's starter will engage and the engine will turn over. Don't do this long... If you can't get the starter to kick over, the problem is most likely with the starter clutch or perhaps the starter itself is bad. More troubleshooting is needed but you know what the problem is... If the starter DOES turn over (suspect it will), then lets do this...
SECOND - test the solenoid... OK... I have explained how the thing works in general. Find the small wire coming in from the starter button... I think it might be a black wire but it probably is some other color. It will be about a 16 or 18 ga. wire. It does NOT connect to the battery lug or the starter cable lug but will have a separate connector on the solenoid. Turn the key ON this time. Take that 12 ga wire and touch one end to the POS terminal of the battery and the connector on the solenoid where the starter button connection comes in. THIS IS A TRIGGER and the starter should turn over. Don't hold it there long as the bike will try and start. If the starting action is quick and positive, the solenoid is good. I strongly suspect you have no problems with the solenoid. If you don't get a strong and smooth starter action, then suspect the solenoid and perhaps replace it.
THIRD... I suspect your starter and solenoid will test out fine. If they do, the problem is somewhere on the path the trigger voltage follows to get to the solenoid. Power goes to your ignition switch via the main wiring harness. It comes out of the switch when the key is on and goes to your kill switch. If you take your right hand switchgear apart and get the multimeter out, turn the ignition switch on and meaure voltage at the input to the kill switch inside the switchgear. Just look for the wire going into the switch and touch the POS/red lead to it and hold the NEG/black lead on a frame ground while the meter is in VDC scale. You should have about 12 VDC. Now you will see where the wire goes to the button inside the switchgear. You can check voltage here. If you get voltage to this point, look at your button. It takes three hands but push the button and check voltage coming off the plate BEHIND the button where the button contacts. This is a very likely failure point but DO check the other places first. If you find a lack of voltage in any of these places, you have found your problem... OK, note the color of the wire OUT of the button contact. This wire runs into a big connector on the right steering neck of your bike which connects back into the wiring harness. Undo the connector and find the PIN on the connector associated with the button-out wire. Still, with the key on, and the button pushed, check for voltage here. This connector often works loose because of its connection. Clean it with the contact cleaner and put some dielectic grease in this connector.
I suspect SOME part of this troubleshooting will identify the problem as there is little esle to check. The button cleaning... you can spray with cleaner but I wouldn't spray with WD40 as this type lube will only attact crud. The most effective way to clean is to unscrew the plate and clean it with FINE steel wool or emory board as it and the metal brad set in the back of the button tend to oxidize and make poor contact. You can buy a new button if the metal brad in the back is worn. I think
www.z1enterprises.com can get them so check if you don't see it on the site.
Your problem seems frustrating but it could have been checked out systematically in about the same amount of time needed to type all this babble and should prove easy to fix once you have gone through these troubleshooting steps. Some of the steps don't provide problem resolution steps so if you find a problem, in say the kill switch, just stop back and I will tell you how to fix the issue if you encounter it.