1. I will only be sailing in the inland waters near Orange Beach and Pensacola. I have no desire to take it into the ocean off shore.
you will take it into the Gulf, don't get a newer MacG, the water balest will not handle well
2. I will only use it for day sailing - will never stay overnight.
3. I will nearly always be sailing alone so need something I can handle by myself.
there are other boats the MacG might not be the boat for you
4. Because the weather comes up fast, and I have a job where sometimes I have to get home a hurry, I REALLY like that I can put a large out boat motor on the Mac Gregor - I can't find another model of sailboat that takes a large motor.
The fact that it is a want-a-be powerboat kind-a-be a sailboat means it will not preform well as ether, look for a 27 to 30 in your area, i am guessing your in the boot heal of AL
5. I would prefer as much space above decks as possible, and the MacGregor seams very small. The below deck is not as important.
Start looking for a Catalina 27 to 30, even the Hunter name will for sailing the Bays and the Gulf coast, don't limit your self to a MacG, and yes i have an older Mac Venture 25.
6. I like that I can take down the main sail by myself on the MacGregor and so I can store it in my boat house, or get it on a trailer when the hurricanes threaten.
The Mast, sure you can but with the right setup you can do so on a 27 to 30 foot Deck stepped Mast.
7. I want it large enough so that it "feels stable".....probably at least 22 but no larger than 32 feet.
then you need at ad some beam to the boat your looking for, my 25 Venture, she rolls a bit, my boat is what Mac Gregor was before the name change.
8. I like that I can beach the MacGregor so I can get out to fish.
you dont have to leave the boat to fish, yes beaching is nice, i dont beach to fish, i still anchor out and wade or swim in
9. I like the price of the MacGregor.
you have not said what price your looking at so from $100 to $21,000, there is a lot of room for more Boat.
So, am I evaluating this correctly, or have I missed something? Anything you can tell me to help me make this decision would really be appreciated.
Let's see you have see a boat that you think fills your bill and it might, Is it the Only one that will?. If all your going to do is Sail the Orange Al to Pcola area then look for something a bit more, you will soon want to spend the Weekend out on the boat and the Mac Gregor will let you, you will also get tired of bending over all the time, look around for something that has a good track record and have standing hear room.
I hope you find a boat that fits your needs, but with the info you posted i will not go more into what I think might fit your needs. for one thing do you know how to sail, are you planning on taking Classes?
Fill in more details so the members might have a better idea as to what limits you have and can then maybe offer more advice to help you beside what boat might fit you best. Fair Wind and have a Good Weekend.
Check the WWW for ASA sailing classes or the the local Sailing Club.