When to start Planning-not training

I'm another "never too early" guy. Some hotels won't accept reservations a year out but you can get on a contact list.

Just curious; if you're in NH, why didn't you go for Lake Placid?

For family vacation, we go away that week.  Not sure the family wants to give up beach time to watch me suffer.   Plus, I will need the extra month of training in the outdoors. 

I don't know if they do this for every IM, but when I registered for Wisconsin they handed out the "lodging" information and made it sound like you had to go through the IM Lodging web site in order to get a hotel room. Which was not true at all. I waited 2-3 months after registering to secure a hotel room, and got a better price than what was listed in their "scare tactic" literature. My family did not get rooms until the month before the race and had zero issues.

But since you said you are a preparation freak, you might want to do it before a month out

Each IM has some unique features. Post on the KY forum to get some tips on planning.

Some races are in rural areas so lodging is limited like LP but others like FL there is ample housing and you can find close and inexpensive lodging the race of the week as it the off season of a tourist town.

KY is a bigger town so you probably have more options for lodging but things close at reasonable prices will go fast.

Consider flying with your bike, driving or sending it with tri bike transport. If you fly and can use Jet Blue or Southwest bike fees are only $50 each way. Other airlines bike fees can vary but are often around $150 each way which makes tri bike transport a nice similar cost option w/o having to take apart your bike.

I had to fly with my bike to IMCOZ because Tri Bike transport doen't do out of country IMs. It was a giant freaking hassle - and expensive, because I didn't do my research ahead of time (Delta charged me $150, I think, each way, to check my bike).

I'd go with Tri Bike Transport. Whatever it costs is well worth the sanity you'll save dragging your bike all over the place !

IMKY isn't like other IM's b/c the demand just isn't there. I was able to book the host hotel on hotels.com for that weekend. I also had friends that booked a hotel right at the finish line 2 weeks b/4 the race for $90/night on priceline. Most other IM's are NOT this ez to get lodging for. Often, it's just as anxious of a time to get a hotel as it is to get into the race. Not so for IMKY. Ditto on the tribiketransport if you are flying to l'ville. TBT service is awesome and worth EVERY penny. I'm using them to ship my bike to Kona in 2 weeks.