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I agree, PDFs don't make a good format to convert from. I acquired a few PDF books when I first got my reader, tried to convert them to epub, it was mostly ugly! So I either read them as PDF or go find the epub version if there is one.
On scanning books to make epub, you will want an OCR software. I run a Win7 PC, so I don't know what's available for Mac, but I have heard nothing but good about Abbyy. I think the pro version is supposed to be pretty good, but I can't afford that. Their little screenshot reader utility came with my little wand scanner and I was quite surprised at how well it worked.
I've just tried the trial download version of Abbyy Finereader Express, and I think it will do well for my modest needs, which are somewhat similar in nature to yours, i.e. I'm converting some childhood books to epub for personal use on my classic Nook WiFi. But, if you can afford it and have more books to convert, the pro version might be better.
I'm just beginning and I don't have a workflow set in stone yet, but what I can tell you is that it is rather a labor of love, depending on how picky you are. I'm fairly picky, so it's not just the scanning and the OCR, but also careful proofreading. I like to proof in RTF, then mark that up so I can switch it to HTML. From there I just drop the chapters one at a time into Sigil (free epub making software).
It's all time consuming though, especially the proofreading. I don't know how extensive your collection is, but be prepared to spend lots of time to convert your books. I'm hopeful that as I go, I'll learn a few tricks to speed things up, but most of what I've read basically says it's not a fast n' easy process.
However, it can be fun reading your old favorites while you proof them, so it's not all bad! And it's a very nice feeling when you take an old favorite that's literally falling apart and bring it to your reader.
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