It is a minimum of 3 days for an electronic delivery of the closing disclosure.

A dumpster costs around $600 and that's the really big 40' x 6', I don't think you could fill 20% of that, but still let's put it at 400-600 (first dumpster has expensive delivery fees) and two days with 4 workers is around 8 man-days (4 men times 2 days), you're paying like 800/day/person (800/man/day * 8 man-days = $6,400 + $600 dumpster), you tell me, is that steep?

You might tip a delivery guy who goes above and beyond but contractors and tradespeople bill for what they do.

This time around , I want to improve my project management flow by having a more formal contract and estipulations as to the work quality , delivery expectation and payments.

You should change up your delivery methods - example: post card one month, email the next.  

An escrow account is an account where funds are held by a third party, for distribution (ie. funds from a buyer are escrowed at the title co. for delivery to the seller a and lien holders, or monthly payments go into an escrow account for taxes and insurance, etc).  

We've staged before and it's about 2k for design / delivery / haul away and 1k a month for rental.

At that point I may offer to pay for shingles and their delivery with payment going directly to the supply house.

If you have the business credit card you get $20 delivery which is a great deal.  

If you are showing up to list a property it is going to matter a whole lot less than if you are schlepping clients around for 8 hours in the back seat of your pizza-delivery beater.