One side of the house is Vinyl and the other is asphalt shingle, It can get pretty strange at times.

They are asphalt shingled gable roofs.

Some people don't think it because their "new roof" experience is having someone slap a 3rd layer of asphalt shingles on.

Hello guys, My tenants wants to have Directv, but when the contractor went to the property, they said the only way to install it would be on the shingles using a tripod type setting for support.

I routinely have to remove satellite dishes from property I buy, sometimes multiple ones, and sometimes on roofs straight through shingles. 

Wear such as granule loss, exposed fiberglass, biogrowth, nail pops, and/or buckling shingles was observed.

It is currently framed out, windows, doors, and shingles will go on early next week.I am looking for some guidance on how you would structure the sale prior to the home being complete.

It could also cost more if there are multiple layers of shingles underneath.  

For example these guys have smaller dumpsters- https://rolys.com/  If you are filling with green yard waste, go bigger, roofing shingles, concrete or dirt, go with a smaller dumpster.

Mark that is a sound idea, do you happen to know if these method is more cost effective than metal or shingle roofing ?