Ive been operating over 20 years, the only time I ever got coverage was if I sold a long term corporate account, cost me about 200 a year for a 1 mil liability policy. The rest of the time I blew it off. I've had 0 issues in all that time. I'm not lucky, I just know my sh*t. If a dealer is that worried about it initaially, thats a big warning sign, (remember this is a used car salesman were talkin about here, enough said.) Then I move on to the next dealer who's more concerned about quality. If they insist, I'd get a signed contract first, then get them a declarations page before I start doing anything with their cars. Also, if its a dealer, they have their own plates, dont get suckered into that BS. In Illinois youll pay a grand a year for IT plates for a dealer that has no loyalty to you in the first place, come November they dry up, give you no work for weeks, then call and expect you to drop everything for some 'emergency'. You run your deal, let the dealers run their own deal. Insurance is great to have, but wont help you get a foot in the door in most cases.