The WWLI/WROR relationship is an interesting one. Keep in mind that the FCC's spacing rules for full-power stations are exactly the same for third-adjacent channels as for second-adjacent channels. WWLI and WROR are already a few km short (68.55 km versus full spacing of 74 km) at third-adjacent, but they're also grandfathered in as pre-1964 licenses. I'm not at all sure how the grandfathering rules for pre-1964 would affect a change from third- to second-adjacent...but if the only issue were WROR, WWLI could specify allotment coordinates a few km south of Johnston and use 73.215 short-spacing to make the move to 105.3 work.
It's WQGN (69 km actual versus 113 km required first-adjacent A to B) and WPTY (151 km actual versus 178 km required co-channel A to B) that kill this one...and that doesn't even get into the question of whether WBOQ would have enough spacing against other co- and adjacent-channel stations even if WWLI becomes second adjancet. Without running the numbers, I suspect the spacing to 104.7 on the Cape and to 104.9 in Connecticut would continue to be an issue. WXLO could be a factor, too. Lots of pieces on that particular chess board.
(Edit: I got curious and started running the numbers on WBOQ-with-WWLI-second-adjacent. It doesn't quite fit, even so - get far enough from WOCN on 104.7 and you're just a bit short to WXLO, and vice versa. WIHS isn't an issue. But it doesn't matter as long as you can't move WWLI, and you can't move WWLI.)