Nickgindy,
Almost 3 years ago I got my GC1715. Your description of your yard size and tree layout is similar to mine and this GC1715 was my 1st diesel unit. But I have 1.5 acres and significant slopes and sidehills on half of it - so I needed 4 wd.
So here are some things to consider:
I got the GC1715 because for about $1,000 more than a GC1705 I got a wonderful seat that is both coil and spring suspended and is really a comfortable and pleasant condition in smooth or rough terrain. In addition - with some easy adjustments and no modifications I was able to considerably change the seat positioning for more leg room and space for boots and heavy clothing (Western WI). That same $1000 got me 2.5 hp more engine capability and more power at the rear pto for equipment choices. And armored directionals. I bought a true mulching 54 inch deck (no discharge chute). That is why I bought the GC1715 instead of the GC1705 but both are nice units.
1. If you love the existing mower cut - why change it ? That doesn't mean the Massey GC products don't do a nice job of cutting (they do) - but a belly mower is a significant investment when you already have a mower that works well and does a great job for you. And if you are going to get married - maybe you're wife would like to run the mower but not feel as comfortable on the GC. Or if you are gone for a couple weeks for some reason - she could still keep the grass looking good on the mower.
2. You already have a snowblower too - and lets face it - you are in North Carolina - not exactly snow country LOL.
3. But there are some things you could add to your GC setup - that would be frequently used (they are for me). I use my bucket about half the time and I have a full set of forks (not bolt on) that I use quite often for moving things, hauling stumps or logs, landscaping issues, etc.. I never thought I'd need forks much - and now I wouldn't do without them (but not clamp-on ones). Lets say you're getting some fertilizer or dirt in bags for plantings - or some bags of concrete or rock - its so much nicer to use the forks with a short pallet to haul much more with less effort. And my forks also can be used on the 3pt so the bucket is in front and still do fork hauling in back.
4. I added a quick attach from MyTractorTools.com where I also got the forks. bucket comes off in less than 1 minute and forks go on in another 1 minute. Also with a quick attach - you can just drop the 155# bucket and leave the fel arms on if desired.
5. I got turf tires so my lawn doesn't get damaged and I get excellent traction in snow and ice even on steep angles.
6. I bought a 40 gallon 3pt sprayer new but inexpensively and if you have trees lining your yard - you'll never imagine how good a quality wand sprayer can work for spraying in an around the trees without getting off the tractor. Then the boom part does the main yard. I don't spray fertilizer - I use it for weed killing or weed/grass killing. No more backpack or hand pump sprayers for me except little areas.
7. Do you need another trailer ? Are you planning on hauling the tractor places other than your yard ? If not - why plan on it ? Now I've driven my tractor on the side of the road many times for 2 miles one direction and then 2 miles back - because I had another place I cut grass and did some snow clearing - but you sure don't need to drive the tractor just to get fuel. A full tank of diesel will last you about 2.5 times what the same thing with your lawn mower will (gas). My neighbor with a 27 hp 4wd lawn tractor - shakes the ground far more than my diesel 25 hp does even though I'm 600+ pounds or more heavier.
8. You mention a dealer that is near you and then you mention a dealer that is 9 hours away. What about dealers that are an hour away? Personally, if you want to negotiate with your local dealer - I'd get some pricing from 25 and 50 miles away - not 9 hours - because he'll take those as more logical comparisons.
9. When I bought my unit - I didn't want the 0% financing because rebates wouldn't happen then. The dealership thru AGCO had 5 more financing choices at various interest rates for various lengths of time and all those used the rebates too. AND - I asked about the AGCO insurance - which my large dealer had never sold before until me. Its an incredible deal price wise and coverage wise because homeowners doesn't do nearly enough unless you add a rider which was more than triple what the AGCO insurance was.
10. Lastly - you're going to get married. So now your lawn is flat and open and tree lined on the outside - but expect she will want some flower beds or shrubs or rock gardens - and it will make your place even better. So factor that in to the idea of a 60 inch mmm consideration. Imagine the nice striping in the lawn with your mower but with easier spraying and weed killing with the tractor. Imagine trimming trees or stumps moving or shrub adding and landscaping with your tractor. And your back being used for other purposes than hauling with a cart or wheelbarrow.