Is it worth investing in both forks and swapping around when need be?
I think it could be.
The road forks will probably work fine at HH and yes they will feel more "comfortable" on the road. The only time I have seen extra rake to be a problem is on indoor tracks at high speeds. It does also sometimes make a bike more prone to "speed wobble". My frame came with some shallow raked forks and the only time they showed themselves was at Newport on the last lap of a sprint at 35+mph, when I swapped out to the regular Alpina track forks, this problem didn't happen again, the bike also felt steadier at high speeds.
I think it could be.
The road forks will probably work fine at HH and yes they will feel more "comfortable" on the road. The only time I have seen extra rake to be a problem is on indoor tracks at high speeds. It does also sometimes make a bike more prone to "speed wobble". My frame came with some shallow raked forks and the only time they showed themselves was at Newport on the last lap of a sprint at 35+mph, when I swapped out to the regular Alpina track forks, this problem didn't happen again, the bike also felt steadier at high speeds.