Or are you just talking about the trim?

Mostly surface cosmetic updates such as new trim, paint, and minor exterior cleaning/fixes.

My father and I are comfortable using tools, and have taken care of some of the work, such as re-attaching gutters, trimming doors, adding downspouts, fixing toilets, etc...

You need to slow down and fully explain your situation if you want valid feedback.The only thing I can say is $200/mo for grass is probably too much unless you were also billed for other services like bush trimming and things like that.For just a cut, you should be paying between $30-$40 per cut if the lot is under a quarter acre. 

All trim, base, and doors we will prep, prime, and paint white. 

Since it was a countertop microwave, I only had to remove one piece of trim to make the swap. 

When asked they told us that closets, trim, and doors are normally extra cost during turnover painting.

Trim up the yard a little better.

Personally, at first glance, I would not take on this project because the exterior, alone, looks like a nightmare of work and cash output and I can't see the condition of the eves, other wood trim, roof nor whether there is a basement that has moisture or water from the melting snow and maybe the basement alone needs serious work and cash to make the house is a condition where someone will purchase it from you.

It would probably be best to actually trim over that big of a gap, as that is a big gap for caulking.