If you're just starting out and needing a lot of tools, Harbor Freight is your friend. As you wear those tools out, lost or stolen, whatever, replace them with a system that's more expensive. It took me a decade to wear out the original cheap Skil tools I purchased. Found an ACE hardware going out of business. Buddy and I bought one of everything they had and it was a good start. I still have a few of them. I started replacing with the Dewalt 20v system recently. So far I've got two drills, an impact driver, reciprocating saw and leaf blower on that system. My son is now on the same system, so if we ever need a quick battery to finish a job, one of us has them charged and ready. I didn't have a real reason to choose Dewalt over Milwaukee. Yellow is easier for me to find in my cramped workshop than red. Otherwise, it really didn't matter. The overall selection of available tools should make a difference for anyone. Most tools available on both brands, I really don't need.

I know I've found off market batteries that work with Dewalt at other locations like Harbor Freight. Not sure if Milwaukee is the same. I also built a new crawlspace robot that is powered by the 20v Dewalt battery.

Character is not developed in moments of temptation and trial. That is when it is intended to be used.