We bought DVC back in 2003 when SSR was being built. I cannot even remember what flyer I received in the mail that made me call that day, but I did...and bought that day. All site-unseen (heck, SSR wasn't even open for stays yet).
We fit the bill, though. We traveled about once a year (or more) and always stayed in Deluxe resorts with plans to continue doing so far into the future.
I knew NOTHING about DVC other than what my salesperson was telling me (and some common sense) and seeing the sales podiums at BWI lobby. And I had never even heard of the DIS or DVC forums and didn't even know resale was an option. That knowledge all came about two years later.
We have had many trips since we purchased DVC (my signature lists them). We have had NO REGRETS other than not buying more points (but resale costs about the same now as what I paid then, so we still might add on).
From my signature, you will also notice that we have NEVER actually stayed at SSR. We typically travel during the first two weeks of December, April, October and November. We always waitlist and have been fortunate to get our waitlists to come through these past eleven years. We are flexible and sometimes are able to book/waitlist at 7 months out and sometimes not. We also always go into each waitlist knowing that it may never come through.
So what does this have to do with your question? Well...
Many on here will tell you to "buy where you want to stay" which is sage advice, especially if you plan on going during crowded times of year (major holidays and summers...you'll need the 11month booking window). And if you have the funds/funding to do so, then absolutely do this. (I'm sure I will get quoted and told that my waitlist "luck" may not always hold out...which again...is true...but....).
If, however, someplace like SSR or OKW looks intriguing on the resale market because of the lower cost per point, that would not be a bad buy either...assuming that you won't be too disappointed if the only option available when you go is your home resort.
ALSO, keep in mind that OKW, BWV, VWL, BCV all have points that expire several years before SSR, AKV, BLT, VGF and soon the Poly DVC. THAT might matter quite a bit to you. I'll be in my 80s when our SSR contract expires, so I am fine owning/buying there.
I say GO FOR IT!

Buy resale to save some money, if possible. If not, buy direct (there are advantages mentioned in previous posts that might make up for the added expense).