I'm not going to be much help because my family had a horrible experience having a joint bank account with neighbors. But just make sure you require more than 1 signature if you decide to go that route.

If you have regular meetings, it might still be easier to just sit down with the bills and have everyone pay their share. No matter what route you choose eventually there is going to be a slacker, so make sure you are very transparent about everything. Visuals (spreadsheets) showing when people have paid/deposited, etc.

Get a quote from a plow company for the cost of plowing 1 storm. Designate one family to be treasurer. Each family upfront pays the treasurer for 1 or 2 driveway plowings - based on how often it snows in your area. The treasurer then pays the plow company for every storm, and keeps meticulous records. At the end of winter, treasurer sends copy of meticulous records and either bill or refund to all neighbors. If somebody doesn't pay, then next year have plow guy plow all the snow onto their cars.

just keep it simple. If you all agreed to share (which is a minor miracle in and of itself) agree on a course of action together. Have a different person be responsible each year. A bank account might be a good idea, make sure it takes two signatures.

Our second home is in a high snowfall location and the snowplow company offers annual contact or an as needed service. We go with the annual contact (about $800.00 per season) and he plows at least weekly and every day we get more than 4 inches. On light snow years, it might be cheaper to go with the on call, per plow basis, but on heavy years, it is a great deal -- I suspect it averages out. In your situation, a seasonal contact would mean one check per homeowner in the fall and then no worries.

I only have experience of shared expenses from having lived in a condo--so did DH before we got married, and my son still lives in one. Even with bylaws, having the condo association lawyer send notice of legal action when payment isn't made, and putting a lien against an owner's condo for non-payment, it still can be difficult to get money from someone if he/she loses a job, or has a financial setback, or is just a deadbeat.

In DH's complex where he was the treasurer, one person had his place foreclosed on during the Recession before the condo board learned of it, and they lost several thousand dollars of unpaid fees because they didn't get involved in time. They almost lost out on another one, but I happened to read the list of tax delinquencies in the local paper and recognized the address so they dealt with it before it was too late. In my son's complex where he was the treasurer, during the Recession about a third of the owners weren't paying their monthly fees.

When I first lived in my condo we decided to manage it ourselves without a management company. I was the treasurer and had to go door to door to collect if people hadn't paid by the due date. Often, it was those who seemed to be the most well off who were the most difficult to collect from and were the ones I had to go see almost on a monthly basis. It makes it difficult to be good neighbors.

Shoveling snow would not put as great a hole in the budget as someone not paying a condo monthly fee, but think about the fact that 2 or 3 of the owners might have to pick up the bill for the snow removal if circumstances cause one or more people not to pay. If you all have enough to cover this, maybe it wouldn't be a problem, but I would want to have EVERYTHING set up so you have legal recourse at the very least.

Anne

If it were me, I would draw up a legal agreement specifying the terms (how you'll choose who clears the driveway, how costs will be split, when people will pay-in, how much snow accumulation requires clearing, what times people need to be able to come and go, etc...) and then have whoever is inclined to do it handle contracting out the work and paying.

I can't see going to the trouble of setting up a special checking account and neighborhood association for this. Can you copy whatever is on your deeds for maintenance, and use similar terms/techniques for snow clearing?

have you considered talking to various services ... i bet its not all that uncommon from their prospective ...

i cant believe any business man.. would be bothered by multiple checks.. he signs them.. and takes them to the bank ... i think you are over thinking that part ...

there is the potential for one of the neighbors to bounce a check ... you could have a small party.. and have everyone bring cash.. and have one person write the check.. if the dude turns down cold hard cash .. do get a receipt ... do go with a bigger company.. rather than Joe down the street ... they will have a reputation to uphold ....

i do favor an annual one time contract ... he either wins or loses.. on how much plowing.. but it forgoes the issue of repeatedly having to pay him ...

a neighbor does this ... after hours from being a police man ... for two years running.. he was doing a happy dance.. due to light snow ... boy did he have hell to pay last year ... lol ... but its his risk ...

talk to at least 3 services.. and i bet a buck.. they will now how to work it out ...

i dont know if all that is worth much.. but the kids are back to school.. and i am so happy .. lol ...

ken

No need to make it so complicated (as long as you can agree on one plow guy!) We shared with two other families and got billed by and paid the plow guy separately. Neat, clean, and simple. We let our fussiest neighbor pick the plow guy. I don't even know how exactly the cost was divided; each of us thought our share was reasonable and consistent with neighbors with single driveways.

A potential problem is if someone upstream from you doesn't pay and the plow guy stops plowing that part of the drive, but a more complicated billing arrangement won't help you in that eventuality--until you sort it out the remaining folks will just have to pay to plow to the street. It's not like big dollars are involved.