All of this can be answered by it "depends"!
Ive got a f 150, f 250, and a DRW f350, They are all older vehicles, all were at the time great deals and were purchased used. The 150 is my daily driver, it just works well for my use. The f250 is going to go, since I will be using the f350 for all my heavy towing, RV and Lance. For me the F350 just does a better job and is a better truck, I get it , its wider and in some instances a bit clumsy but when pulling my trailer or loaded with the camper it really SHINES. So for me, it depends on having a daily driver and being able to use the f350 for the heavy stuff.