Looking for someone to configure site, not much custom PHP

Hello. I am moving my site from php nuke to Drupal, and I am getting a little flustered. I could figure all this out if I had a week or two, but I would rather pay someone to get it set up and then study how it was done so I can expand later. I'm a Peoplesoft programmer so I understand the SQL part well. I have a Drupal book on order, but I thought I would see if any are interested in helping.

This is a site I'm doing for my father, its a community site and the budget would come out of my pocket, so I'd prefer to spend between $25 and $100. I know this will probably chase off the most talented people, but the tasks are pretty simple.

I have the site loaded, many modules in there already, but I'm still confused about views and taxonomy to do things right. I don't want to start off on a bad foot and realize it later.

Basically, it is a site about boats.

Page 1: Inconsiderate Boaters - a page where people can read about user submitted boaters that are inconsiderate. Any authenticated user can submit. Preferred format would be to have a header page talking about inconsiderate boaters, and a list of "stories" below showing user submitted content listed below the header. Each story should have a thumbnail of a submitted image with the teaser to the right (like consumerist.com). Selecting more would take them to the full article. Preferably, there would be a link on the page. Comments would be shown on the "read more" page, but the number of comments would be on the "Inconsiderate Boaters" page.

Page 2: User submitted gallery. Point me to a good module if an ideal one exists. There are so many.

Pages 3-x. Marinas Page. This would basically be one page type that is replicated for how ever many Marinas participate. Basically, it would be like the Inconsiderate Boater page format with the header and a list of story's below. Difference is that the people that are able to submit would be limited by role. I may have one person for Chickamauga marina, and another for Bay Pointe Marina. I suppose the format would be almost identical to Page 1. Oh, if there is no image loaded for a story, the teaser should cover the whole "box". Otherwise, it should be 1/3 image, and 2/3 teaser, if that makes sense.

Navigation: One link to inconsiderate boaters, and another for "Marinas" with maybe a dropdown (javascript?) that shows the other marinas when you hover the mouse over the "Marinas" button.

Forum: Nothing to do here really, I am using the regular forum in conjunction with "Michelle's" Advanced Forum. I think I can handle this part.

Thats basically it. I think we could almost configure existing modules to do this, but ya'll are the experts. I'm already using multiflex-3 theme.

The current old live site is chattanoogaboats.com my test site is horseshoecove.com Thanks.
Jeff