It doesn't sound stupid at all, particularly if you're one of the
people who clearly has spent considerable time getting their diaries
set up to look nice (there's plenty of hideous looking ones around,
the nice ones take work!)
It would be my intention to provide a WordPress theme that is selected
by default and imitates what we currently have with DearDiary. It's
true that I'd probably not be able to match everything there is
currently, in that the current layout uses tables and I'd prefer to
move to a CSS based layout scheme. But I'd aim to make it as similar
as possible. It's also true that there would be some pain involved
because I don't think I could automatically move the customizations -
they'd need to be manually re-done. But, most of your pain and
investment is in the finding and editing of images.
So, the default setup would provide essentially the same look as the
current DD (with better search engine optimization due to CSS instead
of tables) - but it would also provide the opportunity for other
templates to be installed if you preferred. There's heaps of WordPress
templates around (see
www.reviewmacsoftware.com for just one ;)) that
could be fitted in.
So, my list of 'must haves' then at this point is;
* Friends System, with Friends Only Diaries
* E-mail Notification on updates
* RSS Feeds (already in WP so that's easy :))
* Day per page as per current DD
* Ability to use same custom graphics with similar layout to current
DD.