We always took at least 5 months a yr off due to weather, we'd do some side jobs here and there, but I used winter as a decompression time as far as construction went, but had commercial plowing, sand/salt, and salt apps to keep us busy and make money for the vacation time.
Sidewalks, never bid them...if they went with a commercial property job they got bid by the running foot, but I tried to stay away from any places that had them because
1. I don't like getting out of a warm truck to freeze my butt off outside and get covered in snow
2. I don't like getting out of a warm truck to freeze my butt off outside and get covered in snow
LOL.
Around here the grass guy contracts were able to do contracts for the winter season, and they bid based on annual snow fall divided by average events per winter, so if it didn't snow much they madeout like a bandit, it it snowed a ton, they lost their butt..but that's the chance you take doing contracts on an average.
All my accounts were based on a trigger amount that we would show up, and regardless of what the business thought they wanted, I told them we have a 2" trigger, no compromises for the simple fact starting with a higher trigger amount takes longer to remove the snow, and it also is much harder on equipment due to the added weight those extra inches carried. Emergency calls, that you/we always get from unprepared businesses were charged dearly for the simple fact they'd have deep snow, hidden obstacles, and the added time that was required to be safe and move the mass.
Do yourself a huge favor and require salt application, on nasty storms we pre-treated and that would buy us a larger window before we had to roll out, and it also helped prevent snow from binding to the surface so when it was time to remove snow, it chiseled up/pushed off like a champ and left a residue effect to help continue the thawing after we left.
Also, if you can DONT do sand/salt mix applications, it leaves a god awful mess come spring time, depending on EPA/DNR rules in the area you may also have to bid going back in with a skidder/broom attachment to clean and haul it away come spring time, it tears up floors inside the businesses due the grit stuck to shoes/boots, and it's slow acting. Everything we bid was 100% salt app, and we kept our lots looking like winter never happened, in the fall businesses baulk at the pricing, during the winter they are happy because customers are happy and comment on how nice and clean the lot/walks are. You may get some flack initially because after salt app you cant see it, because it's white and blends in whereas sand/salt mix folks can see what you did...but straight salt works FAST, so give it 30 minutes and it'll look like the parking lot was rained on due to being cleared and wet vs patches on hard pack.
I found it easier to charge for salt apps using our tailgate spreaders since I could charge PER bag used, bulk salt is tough since your loaded with 34-3600lbs of salt and have a hard time tracking how much was applied at each lot, so you kind of wung it price wise....The money is in salt apps, charge as much/more than plowing, no beating on your truck like a plow does, and fast...a typical lot that took an hour to plow, took maybe 15 minutes to salt.
But going back to original question, I myself liked billing a per push, that way I knew I was getting paid anytime the trucks were out, the seasonal stuff can work in your favor, but can also work against you...give a customer enough yrs under a seasonal average contract that you come out smelling like a rose, they will and do eventually start looking elsewhere to even the playing field so they're not just throwing money away.
THE #1 thing to remember, don't take on more than you can handle, take enough to make good money, but give them exceptional service so they are more inclined to keep you on board. 17yrs of plowing I only lost 1 account and that was due to new management taking over and they were concerned about losing $60 a winter because another guy bid it less LMAO, and that winter, they weren't cleaned out until long after they opened, and it was a pizz poor job at that, but they saved an average of $60 LOL.