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Great topic! It's a tough question. Making design decisions is an ambiguous pastime - what looks good for some can look pretty awful to others - there is no accounting for taste. With that in mind your question becomes more pertinent - how to compare and quantify a pair of designs in a structured and analytical manner?
I would surmise the best approach would be to head back to the original brief (assuming there is one) and write a mix of targeted and subjective style questions. Then mark each design against them.
Our team here recently used survey software to write a questionnaire that we sent to a selection of staff, clients and contractors asking them for a few moments of their time to give us some feedback on our company website re-brand.
The type of questions we posed were:
Given the brief would you say the design reflects the requirements in a successful way?
What are your first impressions of the website?
What messages does the website initially communicate about our company? We are...
How would you rate our website in relation to other business websites you have visited?
And so on...
The questions included technical ones about colour, system and browser etc too. The results are a little nugget as they actively reflect our marketplace both internally and externally.
Amazingly almost all of the 50 or so people we asked to fill in the survey took part and luckily for me (designer) the comments were generally very positive - the criticism was, for the most part, very constructive as well.
Although this might seem to be asking for trouble, and is a bit nerve racking, the results can be very telling. You cannot dispute 100% of people interviewed liking the design - even if your boss doesn't.
Maybe you could approach your design problem in a similar way - creating a checklist that you are able to mark each site against. And then ask the same of a few respected colleagues or friends. Other peoples views are very important, even if you choose to ignore their suggestion to use that funky comic font you get on windows ;)
All of that said, taking a break, fresh air and a bit of common sense is often enough to make a decision as to what hits the bin.