Personally, I would purchase the 14ft boat. Here are my reasons.
With where I fish, and how I fish, and where I hunt, and how I hunt, a 16 foot boat would be perfect. However:
-A 14ft boat generally doesn't require a title. Therefore, it costs less to legally maintain in my state.
-Legally, I don't need as much crap in my boat (like extra fire ext, life jackets) because it's only 13'10"
-A smaller motor will power it as well as a comparable speed on a bigger boat (bigger boat = bigger motor)
-Therefore, less fuel is used every time I use my boat, and it's cheaper. Currently, my 6hp is great on my 14ft boat and I have yet to refill my 6gal tank this summer.
-The same mentality holds true with electric motors.
-smaller motors cost much less.
-Easier to trailer and store, smaller = less necessary space.
-insurance. for my provider, under my home owner's insurance I have any boat included, so long as it is under 16ft in length and 50hp.
-yet again, EVERYTHING is cheaper.
While yes I would love a 16ft boat, I just don't need it. I always bring 1 other person max with me fishing or hunting, including my girlfriend who lays out on the deck. It's very manageable, and the hull is light enough that I can effectively man handle the boat on the trailer as needed. Overall though, just see what works for you, and go from there.
On a different note, width hasn't been mentioned. a 1448 will have taller sides than a 1436 or 1432. I own a 14ft v bottom, that is pretty much a 1436 jon in size. I would never own smaller, and even a 1436 jon would make me question. My next boat will be a 1542, and I'll likely stop there.