NOW the biggest con imo is the upkeep. Disney imo takes a long time to renovate and upgrade the dvc spaces. the mousekeeping is also lax but I think that's the entire resort system
When I bought in a second time, I bought through resale which was much less expensive and I was able to choose my home resort. You can't use resale for 2 of the exchange groups (I never wanted to use them anyway) and you can't use it on property at a non DVC hotel.
Cons:
Housekeeping every 4 days
Yearly maintenance fee (but compare that to what your trip would have cost without DVC)
Not that I would recommend buying direct, but you can buy direct at any resort you want as well. Your DVC rep will try and steer you to a new resort, and will tell you they dont have points at any other, but if you stick to your guns, and say "I want points at XXX resort, and if I cant get them there, then I am going to walk out" they will get you points at an other resort. They simply exercise their ROFR on a contract that is up for resale at that resort, and then sell it for full price to you. They would much rather sell off the stock of new points that they already own, but if push comes to shove, they will "flip" a contract and make a profit, rather than loose a sale entirely.
As for upkeep and housekeeping being cons. Here is the thing. You yearly dues aer not some number pulled out of the air. They are directly the operating costs of the resort. In fact, by law, they can ONLY be the operating cost. DVC cannot make a proft off of dues. They add up all of the costs of running the resort - housekeeping, refurbishments, money paide to WDW for bus service, life guards, the free family stuff at the pool, free movies, replacing sports equipment, the soap and shampoo, landscaping, etc - everythign. Add all of that up, and then divide it by the numebr of points out there, and that is the yearly dues per point.
So you DVC resort could have twice a day housekeeping, a new paint job every year, and brans new carpeting a furniture in all the rooms - but then your dues are going to go through the roof. I happen to think DVC strikes a very good balance between offering service and refurbishments, while at the same time keeping dues under control.
It's also why people get all up in arms when other people break things, steal things, and generally dont treat the DVC resorts as something that they (and multiple other people) are paying to keep up.