This Tanzer model does not do it for me aesthetically but that is neither here nor there. I think Tanzers are well-regarded and the price point leaves some room for fixup. Also, since it is a well-known make it will be a bit easier to resell at some point. None of the issues you mention should be particularly costly to fix other than the sails and you know where you stand with that. You can get some decent used sails pretty cheaply as well. I would consider an offer in your shoes.
Back to Grenada in early December. Not sure I will remember how to sail. Will spend the winter and early spring in the Caribbean and then head to Bermuda and the northeast US. Still trying to decide if we will bring the boat to Canada, either in 2015 or 2016.