[snip]This year I started getting neighbors giving me some cash. That got me thinking if I should invest in some better snow equipment and expand a little more. Let's not get bogged down in liability,insurance, lawyers, yada yada. I'm not talking about a business, just found a better job for friends and neighbors.[snip]
Not trying to be provocative, but getting paid cash
makes it a business, whether you view it as such or not. Warm apple pie once in awhile is different.

I gather you've followed discussions elsewhere on this kind of thing, and we all have our own comfort zones on risk. But if you're doing 10 driveways off your property as you say, even for neighbors who are friends, and are accepting cash for it, it would be beyond mine to run without at least liability coverage. And that would be even if I were comfortable without physical damage coverage (which your homeowner's policy or typical farm policy won't provide in those circumstances).
Just a fer instance, then I'll butt out: Say you plow a driveway for a neighbor on a sunny 34F day, and there's a little more precip, then a refreeze that evening. Neighbor's 15 y/o daughter orders a pizza delivery. Or invites her 17 y/o boyfriend over after telling him the way's been plowed. Delivery guy or boyfriend slides on the icy driveway and wrecks his (or Daddy's) car, and bang's himself up. When the lawyer's demand letter arrives, it accuses you of negligence for failing to clear the driveway properly, failure to put down rock salt, ice melt or sand, and failure to warn of a dangerous condition you reasonably knew would result from the existing circumstances, yada yada.

Even suits that end up being dismissed cost thousands to defend these days, and that would be all on your nickel.
Unfortunately this kind of risk exists even for those of us who plow strictly as volunteers. But doing the plowing for hire raises the ante, makes the operator even more of a target, and also makes any insurance he/she
does get significantly more expensive :2cents: