Recovering at South Shore is okay, unless you have a strong South Easterly or North Easterly (6+).
As for the good pubs, try "The Windsor" at the top of the harbour, or try to blag your way into the yacht club opposite.
Word of caution - do not attempt "The Hilderthorpe" which is a bit further down the road from the windsor - it is a trawlermans pub and gets quite "handy" most nights - short of that unless you travel to the old town part of Brid, you would be hard pushed to get a good one.
Try these links and check out the forums etc;
www.bridlington.co.uk
or
www.bridlington.net
As for overnighting if the weather closes in - unless you can get secured in the compound at the top of the slip and fix a wheel clamp, removing all electronics etc.... then my advice is sleep on board outside your hotel
Hope this helps.