I am doing Timberman this August, my second 1/2 IM. I'm also a little nervous about the hills, but I looked at the bike profile map the other day and it might not be as bad as you expect when you hear "New Hampshire". I have not done St Croix but it's rumored to be extraordinarily tough on the hills. I would bet that you weren't the only one having trouble!

If you're going to do Timberman, you'd better sign up soon. There are only 50 spots left, and many of the people who didn't make it into Tupper Lake before it filled up are going to be looking hard at Timberman.

I've done Diamondman, the race in Delaware in September. It's run by Piranha Sports and they do a great job at all of their races. It's a lake swim in a somewhat murky (but clean) lake.The bike is flat except for a one mile climb and descent over a bridge. It actually felt good to stretch out my legs on this climb.The run is on nice trails that are mostly shaded and have only gentle hills.

I would highly recommend this race. Neil Semmel, the RD, did a great job for a first time event and it should only get better.

I've done Timberman & Firmman. Firmman: Definitely a local race. Not nearly as well supported. Given that, the support is adequate. It's a fast course (though their changing the bike course this year - good thing if it eliminates any of Rt-1), and a beautiful ocean swim (walk up the beach & swim one way back with the beach on your right). Timberman: well supported, hillier bike course (though I did it 3 years ago & it might have changed), lake swim. Timberman will close registration, I don't remember FIRMMAN ever filling up. Choose Timberman if you want the expo, food etc., like hills on the bike (not nearly as radical as St. Croix from waht I hear (never done St. Croix, but I want to!), but a 25 cog is nice for a 20 mph rider (700cc)). Choose FIRMMAN if you like the coast (beautiful area), flatter course, ocean swim. If you wanted to do 8/17 & 9/7, 3 weeks would probably be adequate recovery, but you could hold back a little at Timberman if you had doubts.

I have also done the Diamondman in Delaware last year. It was an awesome race. The course was great. Parts of the bike and run were very scenic. It was well organized and not overcrowded. The bike, like sevans said, was mostly flat, but had one pretty big climb over a bridge. The run was off-road.
If you do this race, the only thing I would recommend is that you bring an old pair of sneakers with you as there is a short run from the swim to the bike transition on a path through the woods. Could be tough on your feet if you go bare foot.
Let me know if you have any questions about the race.
Good luck in your decisions.

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And the road gets rocky along the way
But if it gets too smooth, it's time to call it a day
-Kinks

I was also thinking about doing Diamondman this year. I have one question for you. Where would you put old sneaker at the swim finish to run to the bike? Is there a mini-T1 (T.05) area where you could leave a pair of shoes?

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- Giving money and power to government is like giving whiskey and car keys to teenage boys.
P. J. O'Rourke

There is a small parking lot (they use to haul boats to the water's edge) just as you exit the water. A lot of people put their shoes off to the side, right near a park info sign. I never would have thought about wearing shoes for this. The day before, at registration, I walked down to check out the swim course. I walked on the path through the woods and didn't even think about coming out of the water shoeless. Some guy down by the water suggested it to me. I was glad to have some old shoes to run the path with. There were a lot of people trying to get to transition like they were walking on egg shells.
It's a fun race. Good luck if you do it.

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___________________________
And the road gets rocky along the way
But if it gets too smooth, it's time to call it a day
-Kinks