I can find out on the trophies. I've got the contact for the place in PA that makes them, as I've done some artwork for the little placards that go on them. Beaver Springs Dragway got sponsors for each class so that they got their names on the Iron Tree trophies as well as the jackets at the end of the year. That might be a 'relatively' easy sponsorship to sell, just to get someone to cover those costs.
Re: Points... these aren't hard to tabulate. Just keep 'em in an Excel spreadsheet, which you can import into the website easily. I did the points for Quaker City Raceway when I worked for them. Wednesday nights were fun times...! It was street-legal bracket racing night. We'd have about 120 cars running, 6 classes. I announced, did the pairings for Top Street, maintained the 100 MPH Club listings, even took pictures of the final rounds from the tower while I was announcing. After the race, took winner's circle pictures, went to the track office, updated the points, 100 MPH Club, and posted race results w/ pics within a half hour of the race being over!
Any way you decide to do the pairings is fine with me. I do prefer *some* kind of a ladder, just so you don't have one lane stacking up because nobody wants to run so-and-so. I guess it doesn't matter to me if you separate S and SS or not... kind of fun to run some people you don't normally get a chance to.