We owned a 258 for ten years. Had a Yamaha F250 (3.3L?) for the first five years. Put 1300 hours on it. Then put on the newer F300 for the next five years. Another 1200 hours and that engine was flawless. More importantly, it had more mid-range power. I never felt the need for more power even when we had several SCUBA divers and all the gear. The F300 even got better fuel economy than the older F250.
We did much of the Great Loop with that engine, We made runs to the Bahamas (with another boat) and many solo runs to the Keys.
My wife preferred driving a single engine and lack of twins did not concern me. We had a float plan, sea anchor, a ditch bag and a good epirb. (But if you're resorting to the ditch bag, it's not a single vs. twin issue.)
I always viewed the single vs. twin issue like this: Either way, if you lose an engine you're gonna have a bad day. With twins, assuming the problem is confined to the one engine (i.e., not fuel, etc.), you can limp home as opposed to waiting for Sea Tow. Then again, it's twice as likely that you'll have that engine problem.