We have rented points twice. We really liked it. We like free dining the best but the dates haven't worked out for us the last two trips. If you want to rent points you can't book until 11 months out. From now until July id just figure out what resort you want to stay at and start looking for a DVC owner about a week before your 11 month window. Most owners want to make a reservation right away and get a deposit.
The first week of June will have a decent crowd bc schools down south will be out, I think. However, I don't anticipate it will be overwhelming. We usually go late August and catch the opposite effect bc schools from the northeast are still out.