Again...go with your gut feeling...you've stated you really don't want to have to do it yourself...you need a better service provider.
A Skid Steer loader can be a ***** in tight quarters because visibility to the rear *****...hence probably why he hit the deck posts.
Your lot is WAY too tight for plow truck to do a good job, and would just exacerbate the problem of a snow pile at the end of the lane...because that is the only place he has to push it off to.
Again, a service provider with a smaller AG tractor (not a lawn tractor !) and a blower would make keeping that driveway clear EASY.
I am sure there are guys in the area with such equipment, and that you've seen them running around. Start calling around now and asking them what equipment they have, then have the guys with the right equipment come out and give you quotes based on your service expectations.
I have no clue what service providers charge in your area...but in my neck of the woods...that size driveway would be about $300 for the winter. The guy comes early in the morning so you can get out, and/or right after the plow has passed during the day so you can get in. typically, if there's not enough snow for the plow (less than 1 inch or so), the guy doesn't come, so you scrape the driveway off by hand.
With a tractor mounted snow blower, there is no pile to worry about, and he can throw the snow wherever there is room.
Imagine something like this clearing your driveway: