Whaler 13 as a first boat for 2-4 people?

SO my neighbor/dear friend and I rent a parking spot next to each other in a little off street, 5 space lot in BK. We’ve been surf fishing for a few months (fishing parking pass) and since we are curious/recreational people, we find ourselves drawn towards wanting to get farther out on the water. Not only will this aid us in our quest to stop fishing for seaweed and rocks, but we are lucky enough to have extra space next to my car that won’t be rented as another parking spot, (about 12ftx20ft to the right of 5 parked cars, in a corner). We naturally got to thinking about getting a 15′ whaler sport. The 15′ proposed size was due to the fact that we both have girlfriends, and we are imagining some other folks will want to get down on some Jamaica Bay/NJ/CT nearshore cruising this summer as well. Weeks of cowardly negotiating with seasoned 15′ whaler sellers later, and we are wondering if we are jumping the gun- asking ourselves if it might make more sense to start with a 13′.

Neither of us have ever owned a boat. It will likely be us two most of the time. We know that deep down, splitting one of these 13′ whalers could end up being a very doable ~3k each. There are a lot of beautifully restored 13 footers nearby for 6-8k. I included some of these boats to show how inspiring the available used inventory is right now. Alternatively, most of the proper 15ft sports/CC’s command 12-18k (understandable- they are badass). Nonetheless, 12k is no longer piggy bank beer money. It starts to be more of a serious investment. Before anyone says, “why a whaler?” We know there are more modestly valued teeny boats out there, but we are trying to have fun with this experience. Being a small part of a classic line of boat history is fun. We are both huge fans of the Montauk and the classic hull shape, and want secure and easy resale value in case we change our minds about this later.

Last bit- We are going to be towing this thing with a jeep renegade (I have 4wd limited with the 1.3L 2019 turbo), so the 15′ boat would be longer than the car and (safely) approaching the 2000# towing limit if the car is full of people and stuff. Rollin’ down Wyckoff Avenue and such. All of the sudden, the boat starts to feel like less of a source of relajao and more of a potential stress-out for the sake of our occasional guests #3 and #4 coming aboard. The 13footer seems like a safer match for the mini jeep. What do y’all boaters of reddit think? Should we just send it on a lil 13′ guy and tell our friends to hold on to the side rails? Will we be able to get out there with four people every once in a while for some low risk hangs? Sorta feels like a 15′ sport, while both sexy and capable, might be a bit too much boat for our first boat, especially if it’s parked in our little BK driveway corner.