Are you on your original battery? If so, it's definitely time to change it. Typically lower quality batteries [try Honda Civic] last 3-4 years and better batteries last about 4-5 years, either way you are at the end of the life span. Colder weather takes more draw and will make electrical issues appear more obvious than in the summer time. I'd avoid continuing to jump start your truck and driving it putting additional stress on the alternator and charging system. You can test the battery for free at autozone but I'd just replace it at this point. 99% of diagnosis are going to do so as soon as you say it's your original 5 year old battery and there are no other associated issues. Alternator issues typically occur while driving as your head lights will dim etc. You can check here for more information on battery issues with ext's
escalade battery issue since not all of them are that simple although most all.
