In your price range an O'Day 25 or Catalina 25 would certainly fit the bill. Both boats offer weekend accomodations. In the conditions you describe, an outboard would be just fine. You could probably get a well worn boat pretty cheap - it sounds like you have the skills to make repairs. One thing to consider is sail inventory. Having good sails really does make sailing a lot more fun - and safer. 10 year old sails are probably going to need replacing unless they were very well cared for. I am not familiar with present day sail costs for these boats, but a new main and jib may run 2K or more. Check it out. I know the Sail Warehouse sells "stock" sails for many popular boats.
These 2 boats have been around for a long time and many were made. I have never sailed either boat, but I am confident that the longevity of their production attests to a reasonably good small coastal cruiser.