Images in Drupal - Future-proof methodology (Image module + imagefield together)

I am prototyping my first Drupal site using 5.10, and have spent 40+ hours researching the many ways of posting images - or at least the top dozen mainstream methods (yes fellow noobs everyone feels your pain on this!)

I want to have a single standard workflow for uploading/attaching/displaying all images on the site, so that I have both maximum flexibility now and protection against the coming changes in how Drupal (core?) will handle them - I don't want to have to do complex data conversions later on, or God forbid manual editing of old nodes.

My proposals and questions will reflect my status as a relative newbie, so please do correct any misunderstandings they may reveal and let me know if I'm way off-base on anything; I understand that these ideas may be overkill, but my main question (Q1) is - will it work, i.e. are there any technical incompatibilities?

1. Set up CCK/Imagefield/Imagecache, define my presets (e.g. tiny, thumb, preview, fullsize, max)

2. Set up Image module, and Upload Image, maybe Image Assist or Inline

3. Create a CCK-based node type (e.g. Article) containing two Imagefields (e.g. image-1 and image-mult). Store the "primary" image for the node (the one that will show in a teaser listing) in image-1 and the rest in image-mult. These will most likely be the images I will base my display design around, using imagecache's derivatives appropriately, and if at all possible I'll base ALL display of these images around these methods for consistency and efficiency.

4. For the SAME Article node, use Upload Image to "attach" ALL of the SAME files. This will then automagically create Image type nodes for each image file, linking them to the "parent" Article node by (I believe) BOTH the method used by Upload module and that used by Image Assist.

This linkage will then be a just-in-case, fallback way of structuring displays if I want to use modules based on Image module's methods rather than Imagefield's.

And these (children) Image nodes will then also be independently available for tagging with taxonomy, linking from or attaching to other nodes, creating galleries, rating/voting etc. if desired in the future.

AND the files will be addressable as files in the filesystem independently of anything stored in the database.

Ideally step 4 can be made to upload the SAME files to the SAME locations in the filesystem as step 3, preventing wastage of disk space. (Q2)

Subsidiary questions:

(Q3) Inline or Asset module for displaying imagecache's derivative images within the node's content body? Or just regular linking to the image files directly from the filesystem, perhaps assisted by FCKedit or TinyMCE?

(Q4) I believe Views will actually let me pick up either/both the Imageassist-linked node images and the Imagefield-embedded ones?

(Q5) I'd like to use Lightbox - any suggestions for compatibility there?

Thanks in advance to any who take the time to respond; once I've organized my notes I'll post a summary here to save others some time.