So Scott,
How does one approach a tree trimming service/company to ask for trees that they would normally cut/chip? How should us Joe's ask for trees we can mill.
Local ares can be real different. The way your city works kinda makes sawable logs a rarity. Here in the Metro DC, MD area wood can be a pain in the but for a tree company. My cousin runs 3 crews and if each one brings in a load of wood that makes a big pile. The labor of processing fire wood got so bad he just quit selling it. He gives a lot away to landscapers he knows that sell wood in the off season. Premium saw logs go to the mill, anything else if you saw them on a job, they would give it to you. He might charge you for time if he had to travel. If you had a place set up with a sloped rig to set the log on, he'd use the knuckle boom and set it on for you. If you called with an interest list he would get back. Call and ask.
For that matter if there is any one in the DC, Montgomery Co area that has a wish list PM me and I'll try to hook you up, Joe.