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When To Change Oil on Lawn Tractor?

I have a Cub Cadet LTX 1050 that I bought in April 2013. My grass is beginning its slow decline in growth, and pretty soon I won't be needing to cut anymore.

That being said, when is the best time to change the oil? Now, before I store it, or when I break it out in spring? Also, is it recommended to add some fuel stabilizer and/or run it every now and then during the winter?

I've done mine in the spring, 14/15 seasons worth.

I do it before Winter each year. I either syphon out the gas or run it until it's dry before storing it.
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"Trust Me I'm The Doctor!" -Doctor Who

Either/Or. Spring is probably preferred, but I usually do mine in the fall so I'm ready to go first thing in the spring.

My concern is leaving the "dirty" oil to sit in the engine for the duration of the winter. Are my fears unfounded ?

I do it middle of summer, once a year, I put about 40 hrs a year on mine...

No, your fears are spot on. The best time to perform maintenance on your tractor is late fall after lawn mowing is over but before winter snow.

Use a quality filter and full synthetic oil, and you'll be all set with engine oil maintenance until next fall. That's the schedule used for my Rider's 22-hp Briggs engine- great results thus far!

Cub Cadet says to change the oil every 50 hours. »www.cubcadet.com/webapp/wcs/stor···ips.html

The oil type is a heated debate on some sites. Conventional and synthetic both have merit. I personally use synthetic 10W30 Royal Purple. I use Marvel Mystery Oil & Seafoam in all my gas containers. I also try to stick to mid-grade 89 octane gas for lawn equipment. It seems to work better in chains saws or when mixed with 2-cycle oil. I try my best to change the oil after the last of the leaves have fallen since I use the mower to mulch the leaves. Most of the time I get it done before Winter but once in a while it sits until Spring. It doesn't seem to matter IMHO. I use the cheapest air/oil/fuel filters I can find. A filter is a filter.

My Cub dealer recommends every 50 hours of operation, but cautions that full synthetic shouldn't be used until after the first 100 hours. Something about "break-in". Synthetics lubricate almost too well, I guess, not giving the rings and bearings an opportunity to "seat in". He does, in fact, recommend synthetic... claims the mower/tractor will run cooler that way. I use my tractor year-round as I have a snowblower attachment for mine, so I just follow manual specifications as to frequency of lube changes.
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Keep your eye on the ball, your shoulder to the wheel, your nose to the grindstone, and your ear to the ground. Now, try to work in that position!!!