ergophobe - 2:39 am on Feb 8, 2013 (gmt 0)
I've noticed over recent years that Google does compensate more and more for common technical issues that websites have.
Agreed (you know I was just making noise, right?). I've recently seen sites with terrible canonicalization, but Google nailed it - doing a site: search showed no non-canonical URLs.
I think that as much as possible, Google does not want to count technical issues against a site - URL canonicalization, code validation and all that - and they have put efforts into overcoming those hurdles. I think these days you have to be pretty messed up to confuse the Google crawler - though in the last two months I saw a two year old personal blog/brochure site for a performer who does all his own writing and it had 85,000 pages in the index according to the numbers returned by a site: search. Must be a hell of a prolific writer ;-)
So yes - Google will do its best to decipher your site. In fact, though people will probably scream at this, I would say that Google wants to rank your site as high as possible based on the content and give as little weight as possible to the technical setup. The technical issues only start to really hurt when you are so screwed up that Google just can't figure out what's what.