Given all the uncertainty, if our early August trip doesn't pan out (which we still may cancel, depending on what reservations we can get, and what attractions they close) there is no way I am making plans for the winter. My worry is that either the Disney parks restrictions will be the same, or the restrictions be looser but a second wave will make it worse to travel then, and more crowded to boot from everyone rescheduling.
Sidebar: I know you didn't ask for marriage advice, but unless you 100% know your wife's feelings about booking travel during a possible COVID-19 resurgence--don't keep this a surprise from her. Even if you guys have tested positive for antibodies and/or are comfortable from a risk standpoint, you still may have to worry about a second round of closures, airline flight cancellations (or bankruptcies), state-imposed quarantines. It's really anything goes at this point.