Jim,
I'm in mid Michigan and am in the exact same situation with three John Deere Tractors(two sixty hp and one small 25 hp).
In my opinion, the answer may vary according to the recommended OCI and unique operating conditions of your units.
I put about 100 hrs. annually on the 2 bigger tractors that have recommended OCI's of 200 hrs. At 100 hrs. thru November, the oil still has plenty of additives to ward off any problems (UOA). I change my oil in March before the "new" season. Here's my reasoning:
1. Plenty of reserve TBN/additives to handle soot,deposits,moisture, acid, etc. over winter. At higher hrs.(maybe +150)I would consider fall change.
2. I dislike an engine/tractor sitting 4 months with zero operation (unless you do the FULL storage procedure) . I start mine up monthly ("warmer day"), run them full throttle for an hour to distribute lube/burn off moisture, etc.. Also, I use my tractors maybe 10 hrs. over winter, so they are not technically in storage.
3. I want to start the new season with fresh oil when the tracor works the hardest. I question the idea of new oil (partially contaminated by moisture and whatever doesn't drain out)sitting four months in the tractor before the work season.
On my small 4115 25 hp tractor I change oil once in spring and once in fall. We use this tractor year round (plow snow). It gets about 120 hours per year but the oil sump is ONLY 2.5 quarts - way too small, thus more frequent OCI's for me.
Good luck and I would like to hear more arguments. Maybe my way introduces more moisture, contaminants, and wear???
With today's quality oils, probably either way works, depending on your unique situation,. A fall and/or spring UOA would tell you about fuel dilution, TBN, etc. to help you decide.