Hello, I have a sad situation to share -- a friend of mine who is a very good painter, experienced too, fell off a tall ladder that did not have "boots" on it. (I've never seen those.) Anyway, do you think he should have asked for boots before painting? Possibly it was a situation where he was shy to ask because he wanted the job... (I don't know all the details.)
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As a painting contractor I find that most contractors charge between $20 an hour and $45 an hour plus paint and materials pending overhead here in Pennsylvania i figure $30 an hour is a safe bet. figure a good painter should be able to prep a 12 x 12 to a 12 x 15 room, caulk, apply 1 or 2 coats to the ceiling 2 coats on the walls and 1 coat on all baseboards, trim, doors and crown moulding in an 8 to 9 hour day. This is with minimal or minor spackling repairs like nail holes and nail pops, not cracks and peeling tape. Thats extra paint is usually  $30 to $70 a gallon pending quality. A room this size will need 1 gallon for the ceiling 2 for the walls and maybe 1 gallon for the trim, doors ext... the square foot price is $1.50 - $3.00 as far as asking for money up front I never ask. If the home owner buys the paint there is no need for money and if your buying the paint and your an established contractor you have an account with your supplier's.  any ways that's my input and guidelines 
Not all people live where they can hire a painting contractor, like you describe. People who live in small towns can only hire painters who have a very small business, and do two or three paint jobs per week. In this case, you do have to be very careful, when you hire a painter, as we have several, in our area, who are out to make a fast buck anyway they can.
Keep an eye on the new cans as they're being brought in. Make sure they look new and don't have paint in the rim of the can. If it's a five-gallon bucket, check to see whether the lid is still sealed on with the plastic strip. The only time it's acceptable to mix water in the paint is when you're using a deep or ultra deep base paint to reduce its stickiness, which is rare with new paint technology. Dark primary colors are composed almost entirely of tint that makes it very hard to work with without adding water.
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The speed with which a painter can complete the job will determine its final cost, but time is difficult to estimate. Some painters have more experience and cover a wall faster, but some are more methodical and take more time. Most painters should be able to cover about 100 to 120 square feet of flat surface in an hour, unless they are working on a very large wall. Wood or plaster might reduce that amount to 80 to 100 square feet. You should also consider the time required for a first coat to dry before a second coat may be applied. This will add time as well -- anywhere from one to 48 hours depending on the paint. 

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