most authorized dealers will do discounts of 25-30%, so with $5k to spend you're effectively within the range of something with a retail as high as $7k, give or take. i'm partial to watches with in-house movements, but you may find the look of the watch to be more important than what's inside it.
if you're looking to spend around $3k, the omega speedmaster pro suggested by the idfnl is probably one of the best watches at that price point. (iirc the base version with the hesalite runs $3,600, but you can easily get one for a grand less than that.) it's not self-winding, though . . . you have to manually wind it every couple days. iwcs are nice, but most of them use valjoux eta movements, which are ubiquitous.
imo jlc, which has also been mentioned, is easily the best value in watches today . . . all their movements are in house, the build quality is only a step or two below AP, patek or lange and they run thousands less (although they obviously don't hold their value as well). nevertheless, they make great watches. the master control and the master compressor are excellent. another model to consider would be the reverso (my favorite), which is a classic that will last you a lifetime and you could pass on to your sons.