The course is MUCH harder than GFT, which has the 1 big hill.
Definitely use a 12/27 or compact cranks.
If you can, train on the course as much as possible. If not, make it a point to come and ride the Horribly Hilly Hundreds (http://www.horriblyhilly.com) 200K ride on 6/17. It will make anything you do after that seem easy. It’s much harder than the IMWI course (probably harder than any IM course–read the web page description), but some of the IMWI climbs are included for your riding pleasure.
Another tactic is to make a weekend trip where you make one day’s objective to ride the 40-mile loop THREE TIMES!!! Yes, that’s 120 miles. For even more enjoyment, ride the 2nd loop BACKWARDS. It’s harder than forwards.
If you have a Power Meter, use it, it will help you manage the rollers. If you don’t, get one ![]()
Finally, plan on it being HOT. The inaugural year was perfect; since then it’s been upper 80’s to mid-90’s. Hydrate accordingly and slow your pace if necessary on the bike.