Hi Brian,
I can appreciate your dilemma. It is very difficult to know which tractor is best for you when you do not have a good frame of reference.
A few years ago I bought my first tractor. I was really trying to get into something for the lowest price possible. I ended up picking up an older International Harvester 28 HP 2WD tractor. It worked well for some things, but I was forever getting it stuck in the mud on my land here in NH (while box blading). Snow removal was not very much fun with it either.
After struggling with it for about a year, I decided to sell it and rented equipment for a little while (mostly bobcats). I figured that I might save money by renting instead of owning - but this turned out to not be true since I needed to rent often - and would usually find an excuse to not do some of the work that I needed to because I didn't want to pay for a rental.
Well during the last few months I decided that I was ready to make another tractor purchase. This time I promised myself that I would get the right size tractor for my needs (lots of landscaping / skidding some logs / brush cutting/ snow removal on 20 acres of New Hampshire land). I still was not sure exactly what I needed.
I looked around at many different dealers comparing prices and trying to figure out which models would fit my needs. The best deal I found (which includes the nicest staff, great owner, and excellent deal on tractor/implements/service) was at Northwood Power Equipment in Northwood NH. They are an Agco / Massey dealer.
If it wasn't for them I would have definitely purchased the wrong sized tractor. They were more than willing to loan me 4 tractors on my land to see which suited my needs the best. When I started out, I was looking at a 4WD 28 HP tractor with a backhoe. Then I moved up to the Massey 1440 tractor to backhoe. When it was all said and done, I decided on the Massey Ferguson 1445 (which actually weighs almost 1,000 pounds more than the 1440 40 HP tractor). I didn't get a backhoe because Northwood Power Equipment has a special rental deal going for compact tractor owners who puchase from them - and let me tell you an excavator rental will do a lot more work than a CUT backhoe!
Some of the incentives that they offered besides good pricing was:
Free pickup and delivery for the lifetime of the tractor
Free 50 hour service ($350 value)
Free 4 year warranty for the tractor
I can't say enough how much I really enjoyed doing business with them. My brother in-law and I just picked up a couple of Stihl chainsaws from them also (I'm kind of addicted to going in there now).
Sorry that this was so long - all I am trying to say is try to find a dealer who is going to work with you and HELP you, instead of trying to just SELL you. You should really work with someone who is willing to send demos down to your land so that you could put it through the paces and see what you really need (and avoid making a costly mistake of buying too small).
The lessons learned from my first tractor that influenced my purchase decision for my new tractor was:
1. 4WD is definitely beneficial when working with a front loader or on snow - my 2WD would just push the front end when I was trying to take turns in the mud.
2. Weight is more important than Horsepower for my uses. I never had a problem with my old tractor due to lack of power (even though it was 28 hp). My biggest problem was the the tractor was too light to put the power to use. My new tractor is 2000 lbs heavier (2000 lbs vs. 4000 lbs) and has 17 hp more (and I would even trade in some of the HP for more weight!!).
3. Service / Support / Parts - I bought my '77 International Harvester used from someone way up in Vermont. I had several problems with getting promised work done and had trouble finding some parts. I realized that I didn't own a tractor to tinker with, but needed something that would be reliable and ready to work when I needed it. Massey is very reputable (and for some reason most of the farms here have newer Masseys), and the dealer is very support/service conscious.
4. Hydro vs. Gear - I was leaning towards gear again when I first started looking. But when Northwood Power Equipment sent me two identical tractors (at the same time), one gear and one hydro - I saw and amazing difference when putting them through their paces. Loader work took almost half the time with the hydro, and I found the hydro much safer when traveling down hills. It was a litte nerve racking filling a huge sink hole that was on a steep hill with the gear tractor, with the hydro it was a no brainer.
I hope that helps a little.