First, IMO you should either try the No Chill method that some people use, or get a better chiller.
Barring that, you can also RDWHAHB and let the trub go into the fermentor.
I don't know what you use for a chiller now. I have a 20-ish foot CFC and it work ok. I'd rather have a 2-stage IC like one of the Jaded models, but that may be in the future when I get done with a few other projects.
Truth is, my anecdotal evidence, and a Xbeeriment, I believe, both conclude that putting trub into the fermentor doesn't really affect beer clarity as much as a good boil, plenty of calcium, the right yeast strain, and the right fining agent.
I believe the reason is because anything that will settle quickly in the kettle, is going to settle quickly in the fermentor (Once active fermentation is complete.) What might not settle well are the microscopic proteins and yeasts. Avoiding some adjuncts that contribute to protein haze (or even excessive dry hopping, but I wouldn't cut back just for a little haze) can help, but darn it, if you need those things to make the recipe, then you need those things to make the recipe, IMO!
Now if you really want to keep more trub out of the fermentor, I'd start by doing a chill, then allowing the wort to settle out some before siphoning into the fermentor. You will lose some of the wort because the trub won't settle compact enough to get all of the liquid off of it in a reasonable amount of time. But if you give it an hour or two, most of it should settle near the bottom and you can start siphoning at the top and work your way down. You will still get some break material, but you can avoid more of the hop debris this way.
I just don't think it's that big a deal, personally.