Yes - your second suggestion would be a better use of the cash, in the order: power meter, clip ons, aero helmet, wheels

how hilly is hilly?
A trainer road subscription and a new tri bike could be a goer! train with power on the trainer, and since its sprints, would you even look at your power meter numbers in a race? Sprint tri's are usually just balls out. Oly's a bit different

You'd probably be faster on a well fitted tri bike with regular wheels than on a road bike with all the things you mentioned getting.

Why not get more of an entry level tri bike that is aero, get a power meter, used aero wheels, and a good helmet?

There are certainly many options, and not one right answer.

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2000' climb in 15 miles

I agree a tri bike would be faster all things being equal.
My thought was between now and then I could train better with a power meter, and would have a lot of fun with new bits for my road bike.
An entry tri bike would just end up being replaced if I wanted to do something longer than oly.

Do you plan on trying to qualify for Worlds? They've changed the Sprint distance to a draft-legal event, no tri bikes allowed, as of 2016. Something to keep in mind when buying a bike, depending on your goals.

Haha nope :)

I'm not 'merican so don't understand these dollars you talk of, but I'm thinking 2nd hand Tri frame like an older P2, 2nd hand deep front wheel (Hed Jet for example), disc cover for whatever rear wheel, power2max meter. Put some nice tires on there. You might be able to add a nice bar and some Tririg brakes. Whatever cheap groupset, 105 or Ultegra.

That's what I'd do.

Why?

Seriously? I do a 12 mile sprint that has 1100 feet of climbing, and that seems like a tun. You would probably be just we well off on a road bike.

Only because I wouldn't be happy with it.

I rode beside a guy same AG in a sprint, who posted a faster bike leg than me en-route to his AG win. He was on a roadie with aero clips and I was on the tri bike. He rode frenetic, like he was on beans, out climbed, out cornered me. But in the long fast straights I would take him back. So it all depends on how fast the courses are and for how long.

But that is not really the issue here I think. A tri-specific bike, setup ready to roll off the rack on any given day, is a lot of fun to ride. So you have the bars low, the wheels "dished" and go for a rip.

Have the road bike setup for training rides and all -round use.

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