Getting two bedrooms in both from mid-June through mid-August is difficult, but not impossible. We got a two bedroom at HHI last summer, but we went in very early June. We might be trying again for next summer, but will shoot for early June again.
How hard do you think it would be to book VB for this October, if booking in June or July? (I likely won't have points until then) I'd be looking for a 2-BR.
I've gotten VB at 7 months for June, July, and/or August every year for the past three years.
I've have not been able to get HHI for June or July all three years. I have not tried to waitlist though - and I tried for a studio (which I hear there are relatively few of).