Welcome Statistic!
How far up the Hudson will you be looking to do your primary boating? As you may know, the conditions can vary greatly depending on where you'll be. The wide open waters of Haverstraw Bay can be manageable but uncomfortable in a 24 footer on the same day that you would be just fine further north. You shouldn't shy away from the size, but before you make a decision based on what seems like what will be a comfortable first step, also figure out what the biggest boat is you can comfortably purchase and own.
I brought my 21 foot Sea Ray Sundeck down to New York City from around 90 miles away in upstate New York when I was much less experienced. While it handled the trip well, it got very uncomfortable as I got into the bigger water and was even a bit scary below the GWB when the swells started to pick up and the harbor traffic confused the seas even further. That trip was the reason I bought my first cabin cruiser.
I would absolutely consider a Power Squadron course or, even better or in addition, a day on the water with a captain. Buy a copy of Chapman's. Now is the time to be learning all of the good habits that will stay with you through your boating life. The size of the boat and where you boat doesn't matter when it comes to good seamanship and safety.
Best of luck with your decision
