Plowing - you are going to probably want to coordinate plowing with the others who will be having it done and use the same service. Otherwise, problems could come up. If the first part of the road isn't plowed, is YOUR service going to go in and just do your part? What good will that do if you come up and the first part hasn't been plowed yet? What if you come up and it's a mess and your guy says YOU are plowed out but the other guy hasn't done the outer section yet? Who do you call? Even if you call the other guy, if YOU aren't paying him, he might not be too responsive.
You will probably get a better price if one guy gets they whole road anyway. Who does the guy in the big house currently use?
House minder services - look in the classified ads on the forum, call a service and ask for a quote. You might get maintenance, pool, and gopher from one place and it would be easier dealing with one provider.
Same for landscaping - check the classifieds and tell them you are looking for a ballpark seasonal cost.
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