I went through this same decision last summer. I have a woods that needed trails, cleaning out, etc. The mowed lawn is about 1.5 acres and we have a garden.
In the end I bought the GC2300 with loaded AG tires and a FEL on it and a 4' tiller. Mowing will continue to be done with a lawn tractor. The AG tires are needed when working in the woods - the turf tires would have loaded right up and just become clay covered slicks.
We are quite wet here also and can easily tear up the lawn. The last several weeks the tractor has become a hanger queen. But soon the ground will freeze and I can get back to work in the woods. Either that or take the floats off the plane and put them on the tractor.
The tiller did wonders with the garden. I did more work in a couple of hours than I could have in a week with a "get dragged around by" tiller. I brought nearly 100 bucket loads of nature's compost from the woods to the garden and tilled it in. Reshaped the garden to eliminate a drainage problem. If the garden does well next season - I'll double the size of it.
My parking area and driveway is paved - one of the best things I could have ever done. The drive is about 200' (quite steep) and the parking area is 60 x 30. I use a plow on my Tahoe for that and a 28" walk behind blower for trim. If we get hit hard and the snow banks get too big, than I'll put the FEL to work.
The FEL is very handy for hauling "things" to and from the barn and for general yard work. Carries the tools, supplies, and refuse. Saves many back aches!!!!
Sure, I could have gotten a giant of a tractor if I had wanted it. But, I got what I felt would do the jobs I have for it, what would easily store/park in the garage, and be fun to operate. A whole lot of the latter!
Orange, green, blue, or red are generally the choices. I went red due to a quickly formed dislike for the two local JD dealers, percieved design problems with the Kubota sCUTs, and the best blue dealer was 70 miles away.
Price wise, they were in the same general ball park - however, the MF did come in about 10% below the other two when I got down to check writing time. This will vary from one locale to another.
My final purchasing decision was based on the dealer. His application knowledge, desire to gain a new customer (not just a sale), and general follow-up.
I notice you are in central NY - near Verona Beach? The first time I became aware of small tractors was passing this place:
New-Used-Tractors-Forage Harvesters-Farm Equipment-CASE IH-New Holland-White's Farm Supply-NEW YORK - although I didn't buy from them (too far from home) I did learn a lot. There is also a really good NH dealer in Richfield Springs (sells Kubota in Oneonta). He was just too far from me - I am near Albany.