I should note,this price does NOT include paint/caulk or filling of nail holes ;(

If I had no overhead, I could install paint-grade molding like that all day for $1.50 per foot(a three piece crown would be x3 = $4.50/ft) and live comfortably. Paint-grade moldings would not be more than $4.50/ft for materials, so I'd say he must have a lot of overhead.
Casey

I don.t know what state you live in, but I live in So. Calif. and I can tell you what I would do here. First, I would get his license number and then check it on the state contractors license site to see if he is in fact licensed and insured and if there are any complaints registered against him. Next, I would ask him for three references and actually go see the jobs. Then I would ask him where he gets his molding. If he has it milled, it's generally better than what you get from a home supply store because it's crisper. I would also find out what kind of wood he is using. No foam or plastic molding. Then, I would have it painted before it is installed. I would ask how he is attaching it to the wall and if he copes inside joints. After this, I would put it all in writing, listing everything I could think of, and have him sign off. Also, a picture from a magazine or such, to have him initial, so you are both on the same page. Then, I would not give him any money until be brought a receipt stamped paid for the material. No money for the labor till the job is done correctly. An indication of a professional is he arrives in a truck with his business sign on it and the license number on the sign. Get at least three bids with references. I would be cautious about a guy that drops off a crew to do the job.

Sounds way high to me.

I would say you should be able to get that type of job done for less than $1000 complete.

I'm also a contractor. Sounds like

Well...adding waste you have roughly 300' of crown trim. You don't mention if it's one-piece or built-up. A 3- to 4- piece install is now 900-1200 feet of material.

Plus material for a couple of doors.

We've seen no mention of site access or photos of the room.

The bid could be way high. Or it could be reasonable. Regional prices can vary. Materials can vary. So a couple of other estimates might be in order.

Where I work, caulk is not an option. Neither if finger-joint.

I will say that with the the call from the car the guy feels he's on egg shells.

But the big variable is the level of detail or the number of pieces in the trim. Single piece versus built-up.

once around the 14x14 room is 56 feet; the larger room 70 feet. Three-part crown would be 378 total feet, allow 10% waste that's still in the ballpark of 400' for both rooms. How did you figure it, mongo? enough "waste" to do a few rooms at your house? jk.
Casey

I might have misunderstood the original post. Based on that photo I figured it was a run of crown at the top of the tray as well as a run of crown where the walls meet the tray soffit. So essentially two runs of crown per room.

With the smaller room being 14' square, I typically get all my trim in 16' sticks. So two runs around the room is 8x16=128'.

The larger room is 14' by 21', two times around the room would be roughly 10 16' sticks, or 160'.

160+128'=288, roughly 300'. Very generous.

Casey, the "worst" room I have in my house is 9-piece crown. So yeah, if my guessing was wrong I could have "saved myself" enough material for a couple of trips around the room with that estimate eh?