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You should redirect it as in your first example. A click on any url  should reach its destination URL within a single redirect. A chain of redirects is creating problems with speed and crawl efficiency.

Every page should be redirected to it's corresponding https page directly.

Hi,

Here is what google says about 404s

"Q: Do the 404 errors reported in Webmaster Tools affect my site’s ranking?
A: 404s are a perfectly normal part of the web; the Internet is always changing, new content is born, old content dies, and when it dies it (ideally) returns a 404 HTTP response code. Search engines are aware of this; we have 404 errors on our own sites, as you can see above, and we find them all over the web. In fact, we actually prefer that, when you get rid of a page on your site, you make sure that it returns a proper 404 or 410 response code (rather than a “soft 404”). "

" If some URLs on your site 404, this fact alone does not hurt you or count against you in Google’s search results. However, there may be other reasons that you’d want to address certain types of 404s. For example, if some of the pages that 404 are pages you actually care about, you should look into why we’re seeing 404s when we crawl them! If you see a misspelling of a legitimate URL (www.example.com/awsome instead of www.example.com/awesome), it’s likely that someone intended to link to you and simply made a typo. Instead of returning a 404, you could 301 redirect the misspelled URL to the correct URL and capture the intended traffic from that link. You can also make sure that, when users do land on a 404 page on your site, you help them find what they were looking for rather than just saying “404 Not found."

http://googlewebmastercentral.blogspot.com/2011/05/do-404s-hurt-my-site.html

I would recommend you to 301 redirect them to the appropriated page  and 404 what you dont find a good page to redirect.