^ This.
Install a Datel (or other similarly accurate) digital voltmeter to directly monitor the charging voltage. Wire it directly from the battery (not from some other power distribution circuit) If you want to install it with a switch or switched relay make sure that the voltmeter is the only load on that switch or relay contacts so the voltage you read accurately reflects the voltage at the battery terminals.
Now you will know (not just guess) what is going on.
Normal charging voltage on the bike with no additional loads is regulated to ~ 14.1-14.3V (even at idle). If you don't have that to begin with, stop and figure out what is wrong with your charging system.
As you add bigger accessory loads you will note the charge voltage sagging, especially at lower rpms. When your charging voltage drops to ~ 12.8V or lower you are depleting your battery, and you may find the battery doesn't have enough power to start the bike after the next stop.
The devices in your list that are significantly large loads are (in order of importance) the Heated Gear, Heated Seats, and Clearwater Aux lights. All of the other devices are relatively small loads of little significance. A 90W jacket liner will draw a full 90W of power, but only when on. If you use a Pulse Width Heat controller (like a Heattroller) it will still draw 90W, but only for a portion of the time that it is pulsed on. You will see the voltage on the Datel dip, then jump back up, at the rate of the controller pulsing.
I was successfull at powering 2 90W jacket liners and 2 pairs of 25W heated gloves on my 1st Gen (along with a bevy of other little insignificant loads like RD, GPS, Starcom1, etc.) because they were on separate heattrollers, and I (unlike my wife) I tend to keep mine turned down pretty low. Worth noting that I could not run that amount of load along with a pair of 50W halogen aux lights (another 100W load) as that would put the charging into battery deficit. I was also not able to run my heated grips (an additional 50W) along with the two sets of heated gear, but could do that when the Mrs wasn't along for the ride.
All of my experience above was with the original OEM 1st Gen stator, which withstood that abuse for ~100k miles. I would not install an Electrosport stator if you paid me to. Just installing a 2nd Gen stator will not boost your output power to 2nd Gen levels. You also need the stronger magnets of the 2nd Gen rotor, which I believe requires a 2nd Gen Stator cover. As mentioned above you'll also need to upgrade to a 2nd Gen R/R that can handle the higher amperage. Someone did it many moons ago. It was expensive, and I'm not sure we ever heard what the full benefits were
Knowing what your charging voltage is makes all the difference in using the 1st Gen alternator to its fullest capability.
