The Food & Wine Festival is in October. So is
MNSSHP. So you might not find too many discounts since that time of year is beginning to gain popularity.
OTOH, there's not much going on in January besides the marathon on the first weekend after the New Year. The weather is not always warm (in fact it can be rather chilly sometimes). But the crowds prior to MLK weekend can be pretty light and there are usually pretty good discounts.