Semi-regular basis you say
Heat is not an issue unless of course you're sitting still. The cure...keep moving.
There are several approaches to reducing the heat. I run RedLine water wetter that has reduced the heat some. It's not, imao, not the header heat as much as that from the radiator, when the fan comes on. Though removing the fur ball does help a bit with the heat, it (cat removal) definitely opens up the sound and power. Personally, unless the ambient temps are upwards of 95+ I don't experience remarkable engine heat; not anymore than any V-twin I've ridden. Chilhowee will be working on engine guard chaps in the near future. Perhaps, because of the forward slanted plane of the OEM guards, this will help to route (scoop) greater air flow along the sides of the engine.
Choose the Rocket III. It's the most bang for the buck
Then adding all that heavy weight tour pack and fairing won't slow you down.
A 180 tyre versus a 240? Avon will be coming out with an offering after the first of the year. Darkside advocates are numerous. I've not gone there yet but I'm convinced. I'm leaning toward Cooper Zeon 2XS. The "rounded mold" profile has gotten my attention. The terrible mileage and outrageous costs of the Metzler are principles in my decision.
Several Captains have added Corbin Beetle bags and fairings. I've not seen an integral trunk offering.