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I'd personally recreate the website or create a new variation and let the website sit for several months (12 months) as it regains it's SEO rankings and keywords. IF it had referral traffic only and no SEO rankings I 301 it and call it a day. After gaining SEO traction there is the chance for a 301 redirect no matter how many domains I have. I've gotten up to 30+ on a single domain and the rankings just keep going up.
However I go the extra long and tedious route of 301 redirecting page by page to the corresponding pages, and moving the content (and updating the content), so the 301 redirect make sense. If you are just buying dropped or auctioned domains and 301ing it, you are asking for trouble.
If there are pages that cannot be 301, I create content on the money domain and then do the page to page redirect. If there is absolutely no reasoning to create the new piece of content, I just do a redirect to the homepage or purposely do a redirect to a 404 page that has a sitemap (or list of resources), and still flags it 404 in the http status (yeah I know, but I do things differently than what your gurus taught you - and that's why I survive).
And what I mean by "SEO traction", I mean getting the site to 1000 visitors from organic Google rankings a day. Anything under that I consider a website that's not worthy in Google's eyes and therefore can cause problems for me down the road. If Google trust a website to send it 1000 visitors a day, then that's a website worthy - that's just my own internal metric. I've seen people do it with higher SEO traffic, I've never seen anyone do it successfully with lower than 1,000 daily organic visitors.
All these pages that you're recreating and merging, etc, are on the money site or the expired domain you just revived?
ex "A lot of times I'll find the most relevant page that **already exists** and aim the 301 there." -- already exists on your money site?
1) you don't care about ranking any urls from the expired domain
2) you just set up the expired domain on hosting so that you can 301 pages that have backlinks going to them
3) you either
3a) 301 those links to existing relevant money site pages
or
3b) if the money site has no relevant pages, you create a page on money site with relevant content and 301 to that page
4) you 301 the homepage if the backlink anchor text makes sense