Well just to be clear...DH one-click is still sitting at 1.6something. So I wouldn't be migrating to 1.7...yet. Ideally like I said in my original post, I would like to get it back to the DH one-click and keep it updated. (and you are right...I couldn't in good conscience and work ethic just leave a 1.0 install behind.)
I have already done what you talked about in your last post...2ce on this site, lol, which is why I didn't want to do it again and was looking for someone here with DH service experience. Because of it's age, it's got a history starting out with html, but it had to be moved to CMS.
It's not the first time a website out-grew it's owner's budget, but as this is more of 'life's work' for the owner, scaling down is not an option. So thanks to your help, I see that I have three plans to consider:
1. Go ahead and attempt the 1.0 to 1.6+ DH one-click, redesign/rebuild the template, remove the guestbook, rebuild any custom menu mods and just slowly deal with whatever content formatting mess there is...one page at a time. (but at least the content will be up there)
- Do a fresh install, (like you said), redesign/rebuild the template, remove the guestbook, rebuild any custom menu mods and re-create every page/article/graphic/link, etc. *Could hire an off-shore company for the data-entry, but I've dealt with the mess from these companies before. Cheap and quick is ugly.
or 3. Go to Freelancer-dot-com. Outsource the whole thing and forget about the one-click. It would be more expensive long-term, but hopefully I could convince the owner to keep it current. We all do our share of pro-bono, but it is still a business. Unfortunately, I don't the client is going to like option 1 or 2, since it means the site will 'look the mess' or 'be missing content' while the budget battles the workload.
Thanks again for all your help. I truly appreciate it!