Ancient battery most likely, which also means cruddy connections, not only on the battery, but also on the starter itself.
Now, back to your real issue- you are saying the truck won't start easily when it's stone-cold? It takes a bunch of cranking to get it to fire off? But once it's running, it works as designed all day, until it gets stone-cold again?
Could be fuel filter/pump related. But more likely the air idle motor on the back of the throttle body. this seems to be a fairly common problem on these late 90's Dodges. My 97 Dakota is included in that mix.
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It's an easy fix, right on top of the engine, and the part is cheap.
But a 5 year old battery? NO way I'd be going into winter with one that old!
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