Orient vs Island Watch
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If I had to choose, I’d go with the Islander. Both are great watches in their own right, but getting a solid watch while supporting an awesome company like LIW would be the clincher for me.
Also Islanders have much better bracelets with solid links, and the lugs are drilled.
Definitely orient,keep in mind you gotta be careful with a black watch as any scratches are easy to see
Have owned the Orient Ray Raven 2-3 times. Great watch but dated
Buy the Islander
I have the Orient Tri-Star with the cal. 469 (which is really just an updated Seiko 7005 from the 1970s) that is my first automatic ever owned. Pretty solid little workhorse, and I've actually got some compliments on it. Amazing since I bought it in a secondhand shop in Tokyo for like 20$ or something.
The Islanders are a lot less dated, and have far newer movements - such as the high beat miyota 9000 series or the Seiko NH36 For 200-300$, the Islanders seem really really nice, but if you can find something like the Orient I got for under 100$, you also can't really go wrong (unless you want a strap monster... do not buy an Orient if you want to have a strap collection since they often run 19 or 21mm bands).
Orient hasn't let me down yet. I think they're a better value proposition as well.
Having a number of both Orient and Islander watches in my collection, I think they are equal value brands in terms of what you get for your money. The differences I can see between these two watches would be sapphire vs. mineral crystal, ceramic vs. aluminum bezel, and DLC vs. PVD case. I think the $136 price difference is fair given the higher quality components of the Islander, and I would probably go with the Islander if I were buying one of these two watches.