I doubt he will find one of those within his budget, the big outboards are very spendy. Mercruiser and Volvo-Penta are the major players in stern drives, service is readily available. Yamaha and Mercury seem to be the current leaders in the outboard market although Evinrude, now made by Bombardier, is back. Local service would be more important than brand, you still need parts doing your own work and you don't want to be waiting for back orders.
The combinations of power and boat style are almost dizzying. For your stated wants I would recommend a bow rider with 90-100hp, they are fast, stable with lots of comfortable seating and affordable. Bigger can be better but how much can the c/c withstand? ;D I rode in one with a custom built 498 c.i Chev marine engine this past summer, we had to be sitting down when he cracked that puppy but I am really glad I'm not buying his fuel.