Love my good ol' boat!
I stand 6-5 (used to be 6-6 but age will shrink you) and sail an Endeavour 37. She lets me walk about below with no shoes on! My head scrapes in the galley, but that is good; my wife has to do the dishes! Ragtime has 2 Quarter berths 7 feet long and the table drops to form another berth 6-10 long and 108 inches wide! This is typical of the "A plan" which has no V berth, allowing a larger galley, salon and head than the "B plan." She weighs in at 20,000 lbs with 8000 lbs of lead in her modified full keel. Drawing 4'6" she can go places many fin keel boats her size cannot. As heavy as she is she does not do well in light air, but she is stable and comfortable in heavier winds, and sails well enough that I have passed a lot of boats that were forced to reef. My boom stands high enough that I have 6-7 under the Bimini, 6-6 under a custom made dodger. The Perkins 4108 diesel develops 50 hp which will push her at hull speed but runs more economically at 5.5 knots. With roller furling, autohelm, and lines run aft nearly anyone can singlehand a 37 foot boat, but I have not added autohelm yet. You can buy one for 40-60K, depending on condition and age, which allows you to add autohelm and other repairs and upgrades within your estimated budget. Another possibility is Hunter 34-5, made in 92 and 93, but the 91 version and 95 version were lower headroom, and the hull is not as sturdy as the Endeavour. I would prefer a stronger hull than Catalina, Hunter, or Bendytoy when offshore, even in the Great Lakes.
I just came home from the St Pete boat show, where I saw the Island Packet 460 center cockpit, with 7'2" headroom. We both wish that was in our budget!