Well, in my opinion...
All the "books" say don't travel alone, bring a tow rope, shovel.....
That being said, I frequently travel alone. The one & only time I had to walk was last month when the back end fell thru the swamp & I was stuck.
You can always break down but preventative maintenance helps. You can't ride for 1000s of miles without needing some maintenance.
Check the clutches, especially the drive clutch weights, bushings & pins.
Check the idlers. Look for broken rubber or bad bearings.
Check for loose bolts, especially on the skid frame.
Check the track tension & alignment.
Check the wear bars.
Grease everything.
Check the belt. Carry a NEW spare. If you use the spare, replace it with NEW ASAP.
Listen for any changes in sounds.
Feel for any vibrations/changes from normal vibrations.
If the speedo quits working on a machine with a conventional shaft system, check for the LH drive axle bearing failure.