I'll be happy to share my thoughts. My personal Ranger is a '94 4-banger (2.3), 4x4 w/ a stick. It's a regular cab & has about 156,000 miles on it.
1. If you're looking at years, try to find a good, clean Gen 3 (93-97) or Gen 4 (98-02). The good news about this generation is that they're plentyful and and can be had for relativly shirt money. I paid about $2,000 for mine in '07.
2. Your only two engine options ARE a 4-banger (2.3 or 2.5, depending on the year) AND a 6 (2.9, 3.0, or 4.0, depending on the year.) Either of the 4's is a good choice, espeaclly if you don't tow. If you get a 6, try to find a 4.0. The Ranger was never offered from Ford with a V8, but some people have swapped them in.
3. Transmissions: You'll get better milage with a 5-speed. Plus, assuming the truck hasn't been abused, the clutch can EASILY last 170,000+ miles. A local parts store used Rangers for deliveries & the manager's mentoind that they get close to 200,000 miles on a clutch under SEVER service! Mine's got 156,000 on the factory clutch & i'm the THIRD owner of the truck!
4. Everything else: Just watch out for the usual stuff like maintaince & rust issues. Ranger's are pretty stout. I liken them to an F-150 that shrunk in the wash. The good news with Rangers is that they're EVERYWHERE. Nearly any parts store will have 90% of the parts you need. What they don't have the local salvage yard likely will.
It sounds like your best bet would be to find a 4-banger/5-speed/2WD Ranger. For winter (as I see you're from Ontario, you'll probably expierence), jst toss about 300 lbs of tube sand & the back & you'll be fine.
Let us know what you find!