It is a lot of travel between ochi and negril. You could take a charter flight, and it would not eat up your whole day (Tim air used to do boscobel to negril), but any of the savings you realized would definitely get eaten by that. Also... While your post said you are doing two chains, the "resort" experience is largely the same between the two. We have done both, and greatly prefer negril. Negril beach is about a million times better in my opinion as well. My wife likes to shop, and prefers the shopping in ochi (well, she used to... I understand it has gone downhill somewhat with the new pier opening elsewhere) in ochi rios to that found in negril. We have gotten some amazing deals on jewelry for her in ochi over the years. That type of duty free shopping is just so-so in negril, with the main outlets in Times Square. The craft markets are very similar.

Our trip this year is split between two hotels. We are doing a week at tensing pen, a small non-AI resort on the cliffs, then 5 days at couples to get my beach fix. Give negril a shot... You will probably never want to go back to ochi.