Nice one, Steve! If we contact LMA, we could mention the possibility of using their photos alongside many others being contributed from the Sydenham Society's collection etc.
The infrastructure (ie hosting, finding & navigating content)
Hosting: I don't think hosting would be a problem; if you have enough webspace we can use yours, otherwise I can allocate part of my webspace to your domain. This proposed historical sub-section of your site could be uploaded to a sub-directory of your site, and re-uploaded whenever updated...
http://www.sydenham.org.uk/history
Finding: A search function needs to be installed, and all pages of the historical section--and maybe other sections of the main site--indexed.
Navigating: Browse Place names, as shown at my test site, seems efficient?
My test site is driven from a database. We could arrange it so that you could send me any text/images, and I can enter that into the Db then generate the HTML pages with all the hyperlinks correlated, as well as resize the images in a batch conversion (fullscreen width = 800 pixels; 530 for thumbnails). Updating the site manually would mean updating several pages whenever a new image is added, so I think it's more convenient to carry on working via a database. I can always send you my software and scripts I used to build the test site.
Some other ideas to consider:
Graphics/Presentation
I see this website is designed by bizz, so Stuart, would you be able to develop a graphical template of what would be a typical Place page of, say, Wells Park Road, using the blue colour scheme within all the tables and borders to make it look as professional as the rest of your site? You could perhaps just tweak one of the example pages from my test site, before sending it to me along with any GIFs or style sheets used, and I can incorperate this into all the pages to be automatically generated from the database and script. Otherwise, I can continue to reverse-engineer this Sydenham Town website, until I get all the cosmetics looking identical throughout (I've already got the gradient table headings looking the same and matched some of the text/background colours).
Maps
Thinking about this more carefully, I think the site would look quite messy with maps; therefore, I suggest, for each photo, to only have the associated map pop-up via a hyperlink. I don't think it would be a good idea to have maps displayed automatically above or below each photo. Each of these maps should be cropped to show only the local group of streets, the building in question, and the direction of the photo.
I think the multiple Standford/OS/Tithe/Drainage maps should not be on every page, but rather, should have their own section with complete global coverage of Sydenham.
Database
The photographic database could be extended to include purely information about buildings; for example, within the caption of a Duke of Edinburgh photo, mention of the Beehive pub--previously stood just to the right--could be hyperlinked to a page containing purely text with no photos, as I don't believe any photos/illustrations are known to exist of this public house? Obviously, we're not writing a book here, but there would still be relevent sections to include as much text/information as Steve Grindlay would like to contribute; previously written articles could be copied and pasted into the database. Each place could have certain fixed date attributes, such as:
*First built
*Rebuilt/Altered
*Demolished
Photos
I don't know how Steve feels about sharing his postcard images on the internet, but a watermark could be superimposed to indicate copyright belonging to Steve Grindlay (as well as in the caption), thereby protecting the image. I actually prefer watermarks as opposed to images that are so small one cannot even make out much of the detail. Not even a scanner at it's lowest setting would result in the typical quarter-screen sized images seen on most websites.
Of course, we can talk about this in more detail when we meet up...