Some questions that will help in deciding if rectangular ports are in your best interest.
What's your max RPM with the current setup? What are you hoping to improve, only top end performance?
What size carb do you currently have?
Reliability should not change at all if the replacement heads are properly installed, with spring pressures that match your cam.
Bigger carb may not help at all, depending on what you currently have and what max RPM you are able to run. Close friend of mine thought he would improve performance on his jet boat by a carb change. I had assembled a very mild engine for him with larger oval port heads and a jet boat cam. So he goes out and buys an 850 Demon carb without checking with me to replace his original 715 CFM Holley (yes, 715). It actually took quite a bit of work on the new carb to get the engine to run as well as it did with the smaller carb, and it never did run any better as much as we tuned on it. His 454 engine could only use so much air and fuel at 5200 RPM, where the impeller let it run.
You don't even have the benefit of an upgraded camshaft, correct?