Things are changing constantly as we learn how to deal with this situation, world-wide. The conditions and requirements that exist today are not really relevant to what they may be in September. We have reservations on British Airways to fly to Italy next September, and I am not going to worry about that until the date is much closer.
We also have reservations for a different trip to Italy next March, and I did make a change in those flights last July based on then-current restrictions and requirements. Again, we were booked on BA both ways (using miles). I booked in April, and by July Italy was requiring all passengers arriving on flights from the UK to self-isolate for 5 days even if they only transited airside at Heathrow. So in an abundance of caution, I canceled the outbound SEA to Milan flight on British Airways (something we can freely do with miles bookings) and replaced it with SEA-JFK on Alaska and JFK direct to Milan on Emirates. That way we will be flying directly from the US to Italy, with no Heathrow transit. But subsequently, Italy removed that self-isolation requirement for arriving passengers with negative tests (and maybe vaccination? I don’t know). So the change was unnecessary——but the requirements could still change again my March, so who knows? Maybe we won’t even be able to go. But if we do—-my husband is thrilled to be flying Emirates (it’s business class with miles).😏
Bottom line is, you are not going to be able to predict the future or second-guess the requirements. Book the airline you like with the connections you like (minimizing connections to one total), and make sure you understand and are comfortable with the cancellation/re-booking terms and conditions.