I started sailing over 35 years ago in high school on an O'Day 22. After college I progressed from a Sunfish, to a Daysailor, to a Catalina 25, Catalina 30 and then our current boat, a Rob Roy 23 yawl.
On your first point, I'd agree with others here that a 30' boat is fine as a first boat - recognizing the higher costs of acquisition, dockage and upkeep; and the inherent challenges of handling a bigger boat - greater weight, bigger turning radius, more complex systems, etc. But a 30' boat isn't all that different than a 22' boat, the principles are the same, just the scale (and cost) is different.
I also agree it's important to choose a boat that matches your primary sailing area. One of the reasons we downsized from the Catalina 30 to the Rob Roy, is that I was transferred from Long Beach, CA to San Diego, and would be sailing in shallower water, and so wanted a shallower-draft boat. In our current waters in Mobile Bay, boaters with drafts over about 5' have issues with our shallow waters.
I just bought a Hermann Lazyjack 32 schooner - I suspect that some of the others currently for sale are among the schooners that you've seen on-line. We're comfortable with the boat's size given our prior boats and experience, and like you I'm really taken with schooners - but I have to say that I'm not sure that I would have picked this for my first boat. This is a BIG boat - it's actually 39' overall, 12,500 pounds displacement, probably around 15,000 all-up, gaff-rigged foresail, 50hp diesel engine, etc. And it's over 30 years old; the survey turned up some issues that don't seem too big to me, having dealt with similar ones on prior boats, but could seem intimidating if encountering them for the first time.
A boat this size can be great fun - we're planning long-range for cruising in the Gulf, Keys, Central American, Bahamas and up the East Coast ICW. But it can also be limiting in some ways. For example, given the length, we're somewhat limited as to where we can dock her; and at $7-10/foot and up, dockage can get expensive fast. I just bought insurance today and it was almost 3 times the cost of insurance for our 23' Rob Roy. Replacing the diesel, when the time comes, can run well over $10,000 - a lot more than buying a new 6hp outboard for a 22' boat. To say nothing of the fact that we spent more than twice what a friend is looking at paying for a much newer, very well kept Hunter 34.
And - heaven forbid you ultimately decide it's not the boat for you - it can be hard to sell; not everyone wants a schooner. Our boat was on the market around 8 months, and I've seen others that have been on the market going 2 years.
All said, I don't want to discourage you - I'm a big schooner proponent - but for a first boat you might want something a little more middle-of-the-road and manageable, to get into boat ownership and see what you really want given the type of sailing you'll be doing.
If you want more info on the Lazyjacks, let me know - there's not a lot out there on the web. Our Rob Roy is still for sale - I'm not trying to sell you my boat (well, not too hard), but take a look at the listing at Sailing Texas, sailing lessons, sailboats for sale, sailboat rentals, charters, sailing videos
or google "Rob Roy yawl for sale" to see any of the many listings I have for her out there - she's also a traditional, split-rig boat that has some shippy allure in a smaller package. Similar boats are the Nimble boats, also a couple on the market right now.
Rob Roy 23 yawl "Fiddlestix"
Mobile Bay, Alabama