Hi Markham. Always good to see a fellow Chicagoan on here. Congrats on your initial weight loss. I just started June 1 at 340# and saw 20 drop the first month. But, I wasn't actually aiming for weight loss (yet), I was aiming to convert my eating to Primal and increase my daily activity. Sihana makes a good point, that I would extend to say that weight loss is going to be a natural byproduct of being Primal, for those who have a lot to lose, as you and I both do. Don't stress terribly.
In regards to your concerns, a couple thoughts and a couple questions. 2000-2500 calories seems way below what someone your size would need, even in a weight loss phase. Your body may think it's starving and holding onto every bit of fat it can. Especially since you've gone off the Paleo way as you say. If you're back to unhealthy (& high carbs), this would make even more sense. What is your eating like right now? And why no more Paleo/Primal?
Also, I don't know much about squash, but it seems like a pretty intensive cardio workout. Which is helpful, but not the answer that most people think. Are you doing any additional strength (bodyweight) exercises?
Lastly, you mention Paleo a couple times, but not sure if you are using it interchangeably with Primal. There are some differences, both in food and PB is a more comprehensive lifestyle framework. If you haven't already, take some time to check out The Primal Blueprint 101 resources.