I would say bring up what you feel is most value to you. Personally, I wouldn't keep beating a dead horse as you say, from experience, it seems exhausting and pointless. It's why I no longer will discuss feelings for him, to him. I'm content with him accepting my love feelings so I will leave it be.

If you truly wanna keep going with it though, then go for it, but just try to remember how it makes you feel when he reacts in a disappointing way to you, do you wanna keep putting yourself through it? I think you would get more value for your money in using him for what aspects he is good at. Just my view though. In the end, it's all your call.