This was the first year I've paid for both mine & my husband's tickets from the same AAdvantage account. Most years, we each book ours individually with our respective AAdvantage accounts.
I usually hold the tix by booking online. We take cruises, embarking in one destination and disembarking from another. So I usually book one way tickets for flexibility. If I need 2 tickets, I see how many are available for the days I want using the booking feature. TIP: if you already have a ticket and find a better one, do not be logged in while you're searching for availability if you're ready to change the booking. I did this last year searching for business class (I already had purchased economy for the same route)....since I had to call in to make the change to my ticket, because I had clicked on the available business class ticket while logged in, the system froze the ticket for a while. Fortunately, my phone agent realized this might be happening & didn't want me to get off the line....and just as we were about to give up, the tickets came back into the system. So we snagged the Business MileSAAvers to Europe!
When I go to put a ticket on hold, I see if there's 2 available. Then I'll either have another computer up at the same time as mine & book pretty much at the same time, or or if there's more than 2, I'll book them one-after-another. In the future, I will probably just book each leg together using one AAdvantage account and the return journey with the other, unless the taxes and fees are more.
The good thing, is you can hold the ticket for 5 days & keep searching for other options (if your destination is in a different time zone, be very careful with the expiration times! I've spoken with agents who've sworn the time was CST but in reality was CEST, a European zone) . You are also able to call AAdvantage & extend the hold as long as there's still availability, if you feel a better ticket will come along and don't want to lock it in yet. In my case, I wait to finalize my purchase as long as I can, hoping for Business or First MileSAAvers.
Enjoy your trip!