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Welcome to the Forums! Here is quick version of a lot of advice.. Forum have had more than 10,000 members over more than 10 years and hundreds of thousands of posts.. First priority is to get familiar with using "search" tab above in blue bar. Click on that, and type a couple key words like dealer discount and see what you find..
That said, yes there are "buying seasons" and it is starting now. Dealers get inventory year round, and get flooring (financing assistance) from Airstream to cover inventory cost/interest for a couple months after delivery (usually..). Factory runs at near constant rate year round (shuts down for new models/changeovers and slows down in winter a little..). So buying as fall units arriving (especially buying units that have been at dealer longer than 90 days..) can result in better pricing on new trailers. Used trailers not quite as seasonal, and dealers generally don't carry much inventory, as they'd rather sell new and provide services.
There are also a handful of dealers that focus on internet sales, strong web presence, and are happy to sell to remote buyers. Other dealers focus on higher margins, look to their immediate sales territory, and focus on trying to provide higher levels of hand-holding, though it certainly appears the internet/high-volume dealers do a pretty good job of customer service as well.. The highest volume dealer is in New Jersey (Colonial Airstream) and others include Toscano in Calif, Northwest Adventures (WA, OR, CA) and Foley in Mississippi. Depending on where you are in Texas, you might visit the Airstream Community (RV Park and homes dedicated exclusively to Airstream owners in Hillsboro. Look for North Texas Airstream Community.. They welcome visitors, and can offer suggestions.. Depending on location, you might save a couple percent of MSRP up to maybe 5%+ compared to local dealers.. Whether that is worth the drive is up to you, but it could be considered an adventure and first outing...
The motorcycle carrier/hitch mount on rear of trailer is generally a very bad idea, as the rear of the trailer is not strong enough to carry a cantilevered load of a couple hundred pounds. You will see them on some motorhomes, but those units are attached to a hitch rated to tow or carry as much as 10,000#.. We have a 2" receiver on our trailer and have been yelled at for using a light bicycle rack and 1 bicycle, though our trailer can handle it with welded frame reinforcements.. If you really need to carry a motorcycle, try either front receiver hitch mount, or get pickup with long bed and perhaps wide ramp/tall doghouse shell cover and carry motorcycle in the truck... Even the Eddie Bauer model Airstream (with lift up rear gate and tiedowns) isn't really designed for more weight inside than a few bicycles or a canoe or some kayaks...
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Condoluminum
In Theory, there's no difference between Theory and Practice, but in Practice, there is usually a difference... 
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