1) Yes and no. Once you figure out a system, just as quick either way.
2) Storage is outside rack, so not much difference.
3) Maybe, but I doubt it. I run messanger lines up the mast and tie them off to prevent mast slapping, same as I do when boat is in the water with spare lines.
4) Maybe, but much more stress with sails up while sailing and the wind does not blow 24/7 all winter long.
5) Thats why you chain those type of stands.
Boats that are deck stepped mast will not get any moisture in the bildge either.
Like I was refering to the OP who is also in my area, 90-95% of the boats in our region, well over 2,000, store with mast up. A large majority of those boats also have cradles rather than stands, which are much more stable. We also don't have a mast stepper, which means $250 to drop and $250 to raise the mast..... so another $500 per year. I would rather put that money to a rigger to go up the mast and do an inspection every few years and save the rest.
In his case, they have a mast stepper, the rig has not been inspected in recent years, so makes sense to drop the mast.
It is best to unstep hte mast EVERY year for winter storage!! There are many reasons for this, but to name a few..
1) A lot easier to cover the boat when you are not fitting the cover around hte mast and rigging.
2) Mast and rigging will last a lot longer (especially if stored inside a shed on racks) since they will not be under strain all winter and they will be less esposed to weather.
3) if mast is left stepped during winter storage moisture can condense on the rigging and flow into swage fittings and crack the fittings when the moisture freezes. Running rigging can slap against the mast all winter causing wear to both rigging and mast. Wind instruments will be exposed to winter conditions shortening their life. There is really no way to keep rain/snow dampness from finding it's way down inside of mast and around the mast into the bilge.
4) keeping the mast in place while hauled out will cause stress and strain to boat since all forces of the wind will be transmitted to a boat that can't "roll with the punches" in other words move to releive the strain. This stresses the rigging, mast, chainplates, etc.
5) A boat with the mast stepped and stored on "Brownell Stands" may be easily blown over i na winter storm damaging that boat and quite possible many others due to the way marinas store boats so close together. Vibrations caused by the wind in the rigging and against the mast can actually cause the stands to move out from under the boat (I've seen this occur) and a strong storm can actually sail a boat off the stands (not sure how that occured, but again.... I've seen a boat that fell off the stands when stored with mast stepped and she definitely "rotated" as she fell, so the bottom of the keel ended up about 4' to one side of the blocks that were under the keel and the boat luckily did not hit the boat on the side that she fell towards)
Of course the worst cases are the owners who not only make the huge mistake of not unstepping the mast but also compound that error by leaving that sails bent on all winter! One good storm and the jib inevitably unfurls.........
If anyone stores ashore with the mast stepped, they better be well insured! Perhaps marinas should start chrging more if owners insist on keeping their mast stepped, a fee greater than the unstepping and storage charge, that would provide funding to cover the greater costs of repair when boats are damaged as they are toppled by a boat falling over.
I would definitely unstep EVERY YEAR unless storing in the water. In the long run it would seem to be much less costly to unstep and prevent problems (or catch them early due to being able to much more easily inspect the mast and rigging) instead of risk leavign the mast up all winter. Contrast costs of unstepping/restepping against the cost of a new rig.
but I did notice you changed it from Midland. 
