What you were talking about could be taken to be nothing else but attempts to figure out the ground rules for "gaming the system". Sorry, but that puts you in an adversarial position. So don't go there.
Here is my advice, speaking as a developer.
Develop your site, for all that it is worth (to you.) Do it without any regard to the ODP at all -- remember that no site is guaranteed a listing at all; and in any case a listing may not be immediate (it might be months even after it's submitted.)
Keep your site together: an integrated site with recognized authority (that is, a local sponsor and source of local information) is, as I say, worth MORE than two splinters of the same site (because it contains more information.) It is worth more to EVERYONE: to the sponsor, the surfers, and us. And that greater value will eventually in some way translate into greater visibility.
Focus: provide more depth than anyone else does, on two or three "local attractions," rather than skimming the scum off the pond surface for a score of them. Later on, you can gradually add the deeper content for more topics.
Differentiate: provide content that the other sites on the subject don't.
Navigate: Make sure your content can be found easily. Link to the sites that do provide content, rather than duplicating it.
Be exceptional. (It is not that hard. A digital camera, a day's sightseeing, and you have a unique record. Do it once a season for a year, and you have an exceptional record.) It is the exceptional sites that are deep-linked.
Be detailed. You want to know how many "tourist guides" I've read that assure me their region is chock-full of plants and animals, and people come to see them? Well, duh! Get someone that knows about the local animals. Get PICTURES of the local animals. Tell us what there is about those slimy mudflats that attracts the animals. Tell us what the animals are up to at night on the mudflats. Don't tell us what's a tourist attraction. Tell us what's unique. And we can decide whether we're attracted. (If you want a sample of what editors would fall over themselves to deeplink, look at the little articles on nature walks in Natural History magazine.) The same racket works for historical sites (include an e-text of an old book on the subject -- instant deeplink!) or cultural attractions. Or museums: ask them for permission to do an article-length review of -- any aspect of the museum.)
Network: If there is a small struggling category on "Mud Flats County Recreation Area" -- try to find more content on it. If an editor in Muddy County/Recreation gets half-a-dozen submittals for MFCRA, he's going to consider building a category, using those submittals and some Googling. And the deeplinks come in from the Googling. Rather than focusing on trying to be the top five sites that appear in Google for "Muddy County Recreation", try to raise the visibility of all of Muddy County on the web -- a rising tide floods all mud flats, or something like that.
Yes, this takes research. But I'm persuaded that any time you want to spend 24-40 hours researching a local topic in depth and creating unique informatioal (NOT promotional!) multimedia magazine-article-class spread on it, you can attract incoming links.
Sometimes it doesn't take much. I have some two-page articles that get links because there's nothing else like them on the web (or, so far as I can tell, in one place off the web.) Sometimes, where there's competition, it takes more. But it's worth it.
Because then what happens? the Muddy County editors start creating subcategories for all the local mudholes. Lots of opportunity for deeplinks, and lots of interested editors Googling for them. And you're in the position of providing selective, premier content.
You won't have to target the ODP: you'll be targeting the ODP customers, you'll be generating unique content, and the ODP will target you.