In my opinion you are thinking too much and sailing too little. Get some experience with what you have and the "advice" you are getting from books and magazines will be easier to interpret.
A few thoughts on your questions:
The ATN Gale Sail is a fundamentally bad idea. The videos on the ATN site are in benign conditions. Consider heaving that thing up on the foredeck with the bow bouncing up and down five or six feet, coordinating with someone at the mast on halyard hoist as you wrap the luff around the furled foresail. Add the bulk of the leading edge of the Gale Sail and you have an inefficient sail that is a nightmare to deploy.
The concept of your smallest sail needing a furler is counter intuitive. Consider a downhaul instead.
If you want a storm sail the advice of your Annapolis sailmaker is good. If, as I infer, you are in the middle Chesapeake Bay, major storm systems are forecast and you stay home. For summer thunderstorms you are more likely to roll up your foresail, reef the main, pull the main in tight, and motor into the wind until it blows through. It doesn't take long.
I agree with the point above that the 150 is pretty big for a (presumably) short-handed cruising boat and a 135 is a better choice, but you already have the 150 so just sail with it.
What sort of boat, how heavy, and where do you sail out of?
sail fast and eat well, dave
beware "cut and paste" sailors.
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