insurance - gotta have it
I'm a property mgr with over 50 comm'l sites and 1.5M sf on book. And if a vendor doesn't have minimum insurance ($1M liab if exterior work, $3M if interior work; $1M auto; $1M work comp or a state exemption cert), they don't even need to bother showing up. Having adequate, or more than adequate, coverage should be one of your main selling points. "Yes, Mr. Customer, my price is a little higher. But I carry $xxxx in insurance and have xxxx yrs experience. Your property is 100% safe with my company." I know that I can get work done cheaper, but I also know that I'll get what I pay for. In over 15 yrs in this biz, I can't think of once that I've automatically given a job to a low bidder just because he's cheap. When I was working my way thru college, I just added a percentage of the cost of insurance to each job. By the 5th or 6th job, premium was paid.
And don't necessarily go with the cheapest insurance quote you get. Cheap insurance can be very expensive if the company doesn't provide good service. Having been involved in the NOLA recovery, I saw first-hand what cheap insurance got people. Jack crap. That's what.
To answer your original question, you will probably have trouble getting a per-job coverage if you don't have a good relationship and history with a quality carrier. If you have a $500K policy and need a rider for $2M for a 3-week job, you'll probably get it. Happens all the time. My primary general contractor carries a $3M liability, but when they work in my 30-story tower, they have to ride it to $5M.
Just my 2€.