Sending a manuscript to editor of journal before submission to journal
Unfortunately  this depends somewhat on personalities so a definite answer is impossible. But if your communication with the editor has been helpful/cordial then it might not entail much risk, contacting that editor. 

But since you already have two rejections where the person was involved, you might want to try for a fresh look at your paper with a different editor. This is especially the case since you weren't encouraged to resubmit with revisions. 

You might also try contacting that editor without sending the paper and just give the title and state that you have revised the paper with advice from the reviewer and ask for any advice they might be willing to give. Perhaps they ask to see the paper. Or not.