If you set aside the idea of "winning", then your options open up considerably. It then becomes an exercise with a goal of whatever you set. Whether that's relaying traffic, having a public display, running contest style or QRP in the woods you define your own criteria for success or failure. The League has made the rules and bonus point structure so onerous it would take a huge group putting forth a serious effort just to be a contender. You're not going to change the League and their agenda so do what you think is important and let the points fall where they may. In this age I would have a hard time keeping a straight face telling the public that amateur radio is a relevant emergency communications resource so it's probably best for everyone if I stick to having fun on Field Day and letting the True Believers push the League's agenda. I'm keeping Field Day fun. It's just a hobby, folks.
I think Mark pretty much nails it when he said "If you set aside the idea of winning". Or at least redefine what it means to "win". If the goal of a group is to get the highest score, then yeah, being somewhere in the backwoods someplace, in a suburb of "wide-spot-in-the-road-istan" is where you need to be. Somewhere you aren't going to be bothered by pesky visitors wondering what you're doing and what's going on, the general public, representatives from served agencies, the dreaded freeloaders mentioned in another thread, etc.
We don't "win" Field Day in the points sense. It's not our goal. Oh, we submit a score and watch for the December issue of QST to see how we did. But it's more of a "we were here" statement, than an attempt to have more points than anyone else. We have the only "open to the public" Field Day site in our county. We deliberately set up in a very public place (one of the Metroparks), in a spot that gets lots of traffic from "passers-by", either on foot, on bicycles, or in cars. And we stop operating to talk with anyone who walks over and looks curious. Then it's back to the "contest" when the visitor is satisfied. Only when someone asks, "why do you do this?" does the idea of emcomm even see the light of day. I would say we had at least 2 dozen visitors judging from the sign-in sheet we had.
A scout leader came by with several of his scouts. They wanted to learn about what we're doing. And they did that by helping us setup.
They learned about antennas, how to erect temporary support structures, and the care and feeding of deep cycle batteries.
We must've done pretty well with them, because the scout leader already wants to come back next year.
Our club mostly does repeaters and public service. Marathons, bike races, that kind of stuff. A lot of our members are "shack on a belt" types. Not that there is anything wrong with that. But there is a lot more to ham radio than FM and repeaters. One of our purposes of Field Day is to expose people to the world below 50 MHz. Let them sit down at a radio and play a bit. When you're used to working 2M FM all the time, getting to talk directly with someone on the east coast, or Florida is big DX. And a luxury once tasted soon becomes a necessity. Seems like every year we get one or two people excited, then they get motivated to upgrade their license. Mainly because we hold our June club meeting at Field Day. Normally our meetings are over dinner at a restaurant. So the June meeting is picnic style at Field Day. Well, we were successful again this year. Two relative newbies are flat out fired up about being able to do at home what we were doing at Field Day. I smell some license upgrades coming. This is what happens when people come out and have "fun" at Field Day. And this is most definitely a hobby. If it's not fun, why do it?
For some of these newer guys, Field Day is probably their first exposure to contesting. So yeah, there will be some green horn mistakes made on the air. As long as they learn from it, it's OK.
Of course the emcomm guys are out as well. The smart ones are sitting in the background, not saying much.
Watching all these people engage in a rehearsal of sorts for "the day after", and having fun doing it.
I'd say we "won" at Field Day!
73 de N8AUC