I would like to put a set of 1.6 roller rockers on my heads but I was wondering if I would have any clearance issues? The motor is a 305 TPI with 416 heads, and the car already has a cam with .444/.444 lift. Would this be too much lift for these heads to handle or not? Any clearance issues anywhere?

YOU WILL DEFINITLY NEED TALLER VALVE COVERS AND ANY TIME YOU INCREASE THE LIFT WITH A CAM OR DIFFERENT ROCKER RATIO TERE COULD BE PISTON TO VALVE CONCERNS AND VALVE SPRING COIL BINDING ... HOPE THAT HELPED SOME

A cam that small won't have any VP clearance issues, and even if they're stock springs (especially if they're aftermarket) coil binding will also be a non-issue.

What will be an issue is the bottom of the retainer hitting the top of the guide boss. Seen cases where .47x would fit, and other cases where it would not. Only ways to be sure would be to either remove a valve spring and measure the distance between the guide boss/top of valve seal, or to install a 1.6 rocker and lightly rotate the engine and check for contact.

Turn off caps lock.

Would the gain even be worth it for what I have done to my car or not?

If you wanted to change lift figures, I would opt for a new cam, rather than rockers. A dual pattern grind would be far more beneficial than just increasing the lift numbers.

Well eventually I plan on going bigger motor wise, and I was just thinking of some small final add ons that I could make to this motor.