The time thing is really a moot point. If someone is willing to put in the time, and money (ON THEIR OWN DIME), to overturn an inevitable medical disqualification, then yea, I want them to at least have a shot. It's not like the FAA is going to select someone else once they reach that point. The FAA will send out their requisite number of TOLs from those who are deemed worth from their ATSA score and call it a day. Very unlikely they'll go back after 4 or 5 months and send out additional TOLs because someone failed their medical. I'm not going to root against someone who wants the job bad enough to go through the FAA's hoops. Don't like the hiring process? That's fine, but don't root against someone who is caught in the FAA's bullshit. We're still going to need applicants in 3 years.
And yes, should they get their disqualification overturned they will get a shot at the Academy, barring any other disqualifying status. Happened to me. I got accepted off the 2015 bid but didn't get to the Academy until 2019 after I got my medical sorted.