I am starting to work on what will be a simple gallery system. (I want to create it myself rather than use the gallery module since I don't need much of the functionality and think that its a great project for really teaching me SS)
That said, I thought about doing it without any modules but wasn't sure how to handle the Holder/sub-holder/image relation that I think I need.
I therefore came to think that the dataobjectmanager with file and image extension might be a good place to work from.
I am however very much a newbie to coding in SS, so I was hoping someone might jump in and lend a hand upfront by suggesting a method of structuring the system.

What I want is:
- a gallery listing page (thumbnail, title, short gallery description)
- gallery page (showing the selected image (default 1st), other thumbnails, image description, photographer, models (can be more that one), and the ability to load the next image via URL params since I want to also add my own ajax loading at a later date)

I guess thats mostly it... any advice would be greatly appreciated?

As the author of the ImageGallery module, as well as that post that seemingly undermines it, I can tell you that what you're looking for is pretty much covered by the functionality of the ImageGallery module, but I think it's smart of you to want to build it from scratch. A gallery is a great way to get your hands dirty with SilverStripe. You'll get exposure to data relationships, custom templating, etc., and that's all good stuff that can be applied to just about any project.

I can help you get started coding your gallery, but I'm a little unclear on your specs. I can't really make out the difference between your "gallery listing page" and your "gallery page".. And what do you mean by "other thumbnails"?

Do you have a mockup or anything?

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ps: I have used gallery before, with the slideshowpro module... I extended it and added templates for monoslideshow.
You can see it running here: gone
being fed and managed here: gone

just thought you might like seeing what I have done with them... (ps: you were great help during that process... and I am getting a much better handle on SS)