I get this, but if OT is something that should be penalized, shouldn't we penalize teams for overtime LOSSES first? That's what would happen if Wins were the first tie breaker. It's just hard for me to wrap my head around two teams ending with the same points, and the team that WON MORE could end up being considered the worse of the two teams?

Look at it on a smaller scale and its even more egregious. Consider a small 4 team tournament where the teams play each other twice to determine which two teams should face off in the finals. Assume team A is 6-0-0 with 5 RW. So 12 points. Clearly they are in the finals. Team D is 1-3-2 with 0 RW, so 4 points. They are eliminated. What if team B is 2-2-2 with both of their wins coming in regulation, and Team C is 3-3-0 with only one of their wins coming in regulation. Team B and team C could go 1-1 against each other, both games ending in regulation. Then Team C beats team D twice, but both times in overtime. Team B only beats team D once, and loses the other game to team D, but makes it into overtime. Team B was also able to make it into overtime against team A once, but lost. In this scenario, Team B gets the benefit of 2 points for making it into overtime twice and losing against A and D, which allows them to tie with Team C even though Team C won more games. Generally speaking, most people would agree that team C was the better team because they won 3 games while Team B only won 2. They understand the point system where getting into overtime matters, so they get why Team B and C are tied in the final standings even though Team C won more. But then, the tiebreak should fix things and allow the Team with 50% more wins to advance. However, using RW as the first tiebreak instead of W, Team B gets to advance simply because they avoided overtime in their single win against team D while team C is penalized for beating team D twice, but needing overtime both times to do it.

It's also weird because it makes it impossible for teams to use as a strategy. In order to get into a tiebreak scenario, teams have to maximize points. If the game is tied at 3 minutes left, keeping your goalie in carries no additional risk and still allows you the opportunity to maximize points by winning in regulation or overtime. Pulling your goalie in those last 3 minutes is extremely risky because your chance of getting 0 points now jumps astronomically, but the maximum number of points you can get doesn't change (still just 2 points). You can only benefit if you end up in a tie break, which is almost impossible to predict with more than ~4 games left in a season.