My first choice for a performance cruiser that would be offshore capable, it would be a J-44. Good sound boats with excellent short-handed offshore records and a great interior layout. In all ways these are far superior offshore boats to either the Sabre or Elan. All they lack are the fancy finishes. With a $300 K budget he can easily buy a J-44 and have $70-80 K left for upgrades and transportation and personal preferences.
If I had to buy one J-44 in particular, I would look at Martinicus Van Breems' (inventer of the 'Dutchman') boat which was beefed up and heavily modified for offshore safety and ease of handling. While this is an older than a late 1990's boat, it has been maintained and upgraded in ways that you would be hard pressed to find in anything newer. For example, it has had custom molded hull, fore and aft watertight collision bulkheads and kevlar collision zones added.
I understand that there was some minor core rot in the deck, but I understand that any deck rot that was found was carefully repaired and beefed up and in doing so the liners were removed and a carefully prepped and painted overhead added, greatly improving ease of maintainance.
When I look at the way this boat has been kept, improved, and equipped I am extremely impressed with the careful and intelligent decisions that have been made.
If I ever wanted to and could afford to own a 40 plus foot performance offshore cruiser, this particular boat would be my number one choice of all of the boats that are out there.