Maintenace costs savings?

We are still reeling from the snowplowing bills for Dec/Jan/Feb. And we are trying to decide what is the least expensive way to cover future lawn mowing, cleanup, general maintenance.

Right now we have a contract for our 12 lot park to mow the common area for $40 a trip (weekly) park is 32 miles from home.

The problem is our 26 lot park only has 15 homes and extensive grass on unoccupied lots plus a large amount of common area. We have not gotten a quote on this yet but I figure the cheapest will be $100-$140 a week! This park is 64 miles from home and 40 miles from other park (but its right on the way).

Plus there is a need for 1 home teardown and 1 partial teardown (one in each park).

Both parks need spring cleanup, about 20 hours work.

These are the options we are thinking about.

1, Just bite the bullet and hire an insured contractor to do this work.

2, Do as much of the work ourselves as we can. But it hardly seems worth it to buy a mower drive 120 mile round trip and mow for 3 hours for $150 savings.

3, Get the required ins, become an employer and hire “employees” (maybe residents, maybe young relative) to do the work and buy some equipment to leave at the parks.

4, Set a young relative up in business, he wants to do this type of work and is more than capable. (pay his liability ins from personal funds) and have him pay us off from his first jobs, then pay him just like any other contractor except way less expensive.

5, Have tenant to do the work with their own mowers, tools and give them free, reduced rent.

I know there are pros and cons to each path, please tell what you have done and how it has worked out.