Hi all,
Hate to say it but this has all been done before, a 23foot cat I bought years ago had this type of system on it, so did many other small cats with cabins I have seen. They mostly had it set up so it could be held in the middle or pulled to windward.

The disadvantages I found with it was difficulty in controlling luff tension on the kite. OK for cruising but from a performance point of view not good. With the tack at the leeward bow, couldn't this allow the leech to end up to windward of the luff when sheeted in causing the side loads to be greater than the forward drive?

I know I am a total racing nut and you may be looking for something else. But in my experience the extra weight and windage of a pole and chute have little effect compared to the time advantages of a quick set and drop. As the speed advantage while the kite is drawing is enormous.
Last season travelling with the Mosquito cats the Taipans we came up against couldn't believe how quick we were upwind with all the gear on, as they had taken their spin gear off believing it slowed them down to much. On a number of occasions we raced with spin gear on against mossies we raced at Titles without the gear and the difference was not measurable.
The biggest thing I found that affected your windward performance with the gear on was thinking about it and your downwind sailing while you were sailing upwind. Once you left the gear on full time and became as comfortable with it as the rest of the boat you concentrated on your upwind and peformed as normal.

Regards Gary.