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You are a hardy badass rider!
You need to check what weight oil to use in cold weather, and like said above -
You need a CCA battery that will do the job.
Yeah, it doesnt hurt it at all. Makes sure the battery is at top voltage. Many of us do this.
if you are reading 14.2 14.7 atvtgecbattery when the motor is running. And you are riding it got at least 30 minutes after starting it, and the battery is dropping below 12.7 is sounds like another bad battery. Best to have it load tested.
if the battery is OK check all your connections to the starter and to the transmission ground.
Are you on a touring bike that has a volt meter on the dash ? If so, keep an eye on that gauge and how many volts it reads. When your voltage regulator starts to go out, it may charge way over voltage and then under. That may be what is killing your batteries. If the voltage is constantly under 14 volts then the stator may be shot. If neither are the problem, then you might have a parasitic draw in the system.
Also, your tender could be going bad.
A further thought is to strip, clean and coat with dialectric grease all your main power cables, at both ends. If any damp or corrosion has got in there will be an extra load on your starter, to overcome extra resistance. Also change your oil to winter weight!
My first Harley was a new FX 1200 with kicker only. I change trans and engine oils to winter weight, to give me a chance of starting the darned thing on cold days! Be kind to your starter and battery....
Update: still riding the bike, and it’s warmed up a little the last 2 mornings (45*f). Checked battery voltage after keeping it off tender. The battery held its charge. Went through like Mr Brown suggested and necked all the obvious connections. Winner, winner. The battery cable to the started was about 1/2-3/4 of a turn from being tight. Bike seems to jump to life now; even after multiple repeated starts. Thanks to all for you suggestions, and advice.
At 33 degrees 20w50 oil is like syrup, that's a big part of your problem. No harm in plugging in the maintainer daily, if the battery doesn't need any charging it'll just turn itself off. I'm in the same habit, when I'm not riding it gets plugged in.
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