Maybe a little late in the conversation here, but here is my $0.02 anyway.
I have bought new, used, crap needing refurbishing, inboard, outboard, aluminum and glass. My first was homemade wood. One of my current treasures is wood, wouldn't trade her for any money, she was out with the family today, but that's for another story.
IMHO, brand new, fiberglass outboard, entry level is what you should buy. Today entry level doesn't mean junk. It just means smaller, fewer amenities and not the biggest motor available.
Mt buddy bought one just like that. He was clueless about upkeep and maintenance, and when he sold it is was crap. But you couldn't tell. A neighbor had a clunker sitting in the driveway uncovered for 3 years, unused. He cleaned it up and polished it , put it in the garage and advertised it as garage kept. It sold in a day. That's what you run into with used - you never know.
My "old" boat was bought brand new 33 years ago. Its worth more now than I paid for it. Depreciation.....pfffft. If you keep it long enough you made a good investment.
My "new" boat came with a 2 year warranty. The dealer extended it to 5 years. Awesome purchase and awesome dealer.
My last used OB came with all kinds of guarantees. It ran only 1 time. The final cost to get it in shape was twice what I paid.
Yeah, the 2footitis guy that sells his pristine baby, or the guy (bless his heart) that sells his baby because he just got deployed to Afghanistan are surely out there. Buy new and you don't have to worry.