no, ryan you are far from a late bloomer. this time last year i didn't think much of vacuums at all but a run of the mill appliance. a year later, i have 6 kirby's and 3 hoovers, nothing newer than 1985. i'm 27 and have only been into it a year. since the start i got into restoring and repairing my own vacs to as new condition best i can. thankfully old kirby's and hoovers are easy to repair, though having servicing manuals do come in handy if you don't know a collector who repairs his own machines to learn from. cosmetic restoration is a story for another thread. i also have a connie 86 from 1958. runs like a dream.
i would check craigslist, estate sales, as well as thrift stores and ebay for connies. i got my connie free from my friend Sean and he found it at a thrift store for $5 with everything. don't fret, and don't overpay. except for my kirby classic omega, i've never paid more than 45$ for any machine i have. average is 25 or less excluding shipping.
like your affinity with connies, i like vintage kirby's and hoovers. hoovers grew on me from this site and the old convertibles and other 50's - 70's era hoovers are great, i have 2 convertibles. however, the heritage II kirby is what got me into kirby's from my friend who had one. i liked how it looked and thats when it all went downhill after i found one of my own at a thrift store for 20 bucks.
you'll find different brands you didn't know much about before visiting here you'll start to like from seeing other's collections here, and take on a few (or like many of us here, more than you have room for) of your own. for the brands you already are familiar with, there are many experts here including myself who know about thier specific brands well and will share thier great knowledge in fixing them up, histories of brands, and how to find parts or what is "oddball" or rare about a brand and certain models.
you'll have a great time here, and just wait till you go to your first mini-meet! i'm going to my second in a few weeks. they're a blast.
Will Hemb