If June and August are your preferred travel times, you want a use year that is
June or prior to June - possibly an April use year. The idea is that if you have to cancel that your points still have a usable 'life' for you to rebook. Once you have points, 11 months is built in - for a June reservation in 2019, I could have booked in July of 2018 and used 3 different use years of points to make the reservation if I had them available as in not already used them. That's where banking and borrowing comes in. I could use 2018 banked points, 2019 same year points and I could also borrow from June of 2020's points - why you want time if you have to cancel, as the 2018 points, once banked would expire by May 31, of 2020.
Booking and use year are two different things. If you have points available, you can book up to 11 months out. This is important at many of the resorts for the peak times mostly. Vero is peak during spring break but easier to get in June. Aulani seems to almost always have rooms available. These are two of the easier to book resorts.
Since most resorts are at Disney, DVC points are best bought for a WDW stay, not a Vero, Aulani, trade out,
DCL stay. And, if you have a preferred resort at WDW, that's the one you should buy at.
Also, do not discount resale. Resale can be very cost saving. If I were looking to buy in to an existing resort, I would be buying resale, in combination with a 25 point direct purchase to get the direct benefits of the minor perks DVC ownership offers - which by the way can disappear at any minute.
Since DVC is a purchase of an 'interest' versus a lifetime, I would look at how long you expect to use DVC. I'm 65 - my resorts will not be mine when I'm approximately 88 and my heirs will not have to be saddled or blessed as the case may be by inheriting my points. So, buying SSR if you want to use for Aulani which expires in 2054 (if I remember correctly) may be a better option for some, or for an older individual buying a resort that expires in 2042 might be the right move.
Take your time and read. The Timeshare Store which sponsors the Dis DVC boards is a good source of info as is the DVC boards. Don't jump right in - it may be a costly error and may not save you money. On the other hand, it might be just what you want. Its definitely an individual decision. This can all be extremely confusing at first look.
edited for missing adding 'June' to my first sentence.