IS is good for adjusting for photographer movement- for sports it's generally turned off- as you really worry more about subject movement and it slows down AF. For nature, it's useful for birds in flight, so if you want to do BIF pictures, it'll take you from about a 20% success rate to about an 80% success rate. Over a ten year lifespan, it's $5/yr- but it increases weight and complexity. Only you can make the choice of if it's right for you.
Most small LowePros won't take a lens the size of a 300/2.8. For nature work, I highly recommend anything that will allow you to keep the lens attached to the camera, in the field, setup time is the difference between missing a shot and not, and while most of the time you'll want the tripod over your shoulder already extended, that's not practical if you're going 5-6 miles with 35-45lbs of gear.
A 300/4 needs twice as much light as a 300/2.8- that's a deal-killer at dawn and dusk when wildlife is most active and the light is at its lowest. Depending on the time of year and your latitude that's 20m to 40m extra of shooting at each end of the day.
I'd really suggest you skimp elsewhere if you can. A 300/4 with a 1.4x is going to be a 400/5.6- no subject isolation, slower AF, and needing more light- that's fine for mid-day shooting, but not ideal for anything else.
KEH currently has one used Sigma 300/2.8 in EX condition- $1539, which isn't much more than a Canon 300/4. That'd just leave you needing a good tripod, monopod,tripod head and QR system. Add in a TC or two for baseball, and you're pretty-much set.
Personally, I'd hold off on the 40D before I skimped on the lens- a 40D will give you about a stop's worth of noise difference, but not the subject isolation AND when you eventually upgrade to the 40D or better, you'll get the faster AF from a 2.8 lens than from an f/4 lens and that extra stop of noise means shooting two stops faster- where if you go with the 40D up-front with the slower lens, you're going to be limited by the lens and it's going to be as good as it gets. By the time you get good with a 300mm and sports, it'll be time for the 50D anyway