Be careful when it comes to looking at a boat to determine its construction. The finish work may be nice but that is not the only measure of work. I would agree that the striper is a notch above a trophy or campion, but I would disagree about it being better made than arima ( I own an arima and they are not fancy but they are very well built). As far as being on par with a grady, well they are not in same league. The grady is a lifetime boat, built to be used everyday for as long as you live. You pay a great deal for that quality, but the resale shows they are generally worth it.
I have an outboard 4 stroke and love it. I hate giving up room to I/O motor box. As far as maintance there is maintance on both. I will agree that there is more on a 4 stroke outboard than a 2 stroke, but there is also quite a bit of the same maintance on an I/O as the 4 stroke. It is easier to change the oil on my 4 than an I/O, I don't have to lay on my belly to change the plugs, and I never have to change the coolant. I have never had to work on my motor on the water (knock on wood

) but if I were in trouble I have a VHF and kicker to get me home. I am not much of a mechanic anyway so anything beyond the very minor is beyond me. Also take a look at most guys that run charters in smaller boats and they all run outboards. I am sure there are many reasons for this including sponsorships but if they were not reliable the charters are not going out and the guide loses a day of work.
good luck!