Fuel, lubrication, shocks, moisture all key concerins
Water in the gas is bad, for boats water in your under water gearbox on your outboard is just as bad, imagine the next time you want to put your boat in the water and finding that the fall befor ther had been water in the gear box and froze and burst the whole thing so you have to replace it. so each time before you put your boat up for the winter while its still warm change out the gear lube with new.
also drain the carburatoir bowl's, the next time you dont you will discover all sorts of white nasty stuff in ther, I like Polaris because they have gereasable drive bearings, dead shocks are bad as well keep them in good shape and wipe down the shafts with a good oil, for coastal guy's was a water clean, get the salts off
dont be afraid to pull an engine or undercarrage, I use a electric impact driver to pull the tunnel bolts when by myself, I use a cargo strap and a 1/2"pipe to lever in alingment the undercarrage when remounting.
I find that when traveling on the trail Ive seen that basket sleds fish tail really bad especially at high speeds, Ive even seen them turn turtle and drug for 400 yds before they righted them selves the driver never once looked back during this, this breaks stanchons and runners, its key to have a properly mounted brush hoop up front this acts as a skid when they are drug a little ways if the front end the runner diggs in to a frozzen tussok it breaks the front the runner.
I like Sigland sleds with runners and the skag this pretty much keeps them traking well, they seem to travel well with a little bit of weight in them, Ive never seen one float up(Kite)or turn turtle.
I fuel my fuel jugs 1.5" from toped off and use plastic bread bag under the cap.
if you leave allot of air space in the top the jug this allows the fuel to slosh the colder it is the more dense the fuel is, dense fuel moleicules rubbing against each other builds static charge, gassing right out of a freshly shook jug spout into a plastic gas tank is asking for a static electric discharge and in some cases leads to a gasoline explosion/ fire on the trail, Ive seen one Guy from up river that was badly burned beacuse this.
House heating oil tanks its futile to install Goldenrod filter vessals they require pressure to feed through them, I use mine as a mud leg and leave the filter out, if you gravity feed your monitor/toyo stove with a goldenrod filter you wont get enough fuel to flow through the filter to keep the heater running much above medium, blow out your fuel lines and replace the felt filter every fall, block your fuel tank so it's water sumps away from the the fuel feed end, never tip the tank to the feed end for that last dregs of fuel (you dont want the contamination problems involved) I try to keep at least 1/2 tank during the winter never less than 1/3'd that fuel reserve may be the differnce,think if your called away unexpectedly for a week. replace the burner nozzle each year, keep a spare nozzle close buy, replace the drive coupler as well, the igniter electrodes should be sharp, not burnt off blunted stubs, clean out the exchanger's too, use a good brush and a shop vac it out so its all nice and clean so the boiler can breath, I find that a good old fashoned boiler is expensive to feed but then again they are simple to fix, if you heat with modern technology you have to keep a extra heater, least a circuit board, if you live in a village you may want to get a surgesuppressor for it,