Speaking from experience (it's actually my son's 4th birthday today), I was always an owner of the two door before my son was born. I did not enjoy putting the infant carrier seat in and out, and when he got big enough for a "normal" car seat, it was sort of a pain to get him into it. I traded in my two door for a four door just after his 1st birthday and no regrets. The 4 door 2nd generation Explorers are about 10" longer than the two doors and I find they handle better as well.
I have always liked Exploders in the winter, two or four door. They handle it well. I've got dedicated snow tires for mine (it's a full time AWD version of the Eddie Bauer). VERY stable in the winter. Obviously you'll lose a bit of control in the 2WD but it should be able to handle most of what you throw at it.
The second generation of Explorer goes from 95-01. I'm never a big fan of a vehicle in its first year of a new generation so '96 should be OK. I owned a '97 Sport (two door) and had it leased for 2 years. It was rock solid. Hard to compare to the one you're looking at because mine was automatic and had the more powerful SOHC engine (not available on the 5 speed manuals anyhow). The 4.0 OHV is a solid performer however and assuming it's been taken care of it should treat you well.
Welcome to the site. I've owned 4 Exploders (all 2000 model year and earlier) and can't bring myself to drive anything else (including 3rd or 4th gen). This site is by far the best Explorer resource anywhere.