I love the way Outlast corrosponds with Whistleblower, so I decided to do a timeline detailing just how exactly the timeline works. Please note this is just based off educated guesses and is not official, just how I think the timeline works.
Whistleblower: Underground Lab: Unknown (x) time. Waylon sends an email to Miles and does his engineer job for 5 minutes before being caught.
Whistleblower: Hospital: x + 2 hours. Waylon is put into the Morphogenic Program and the slaughter begins.
Whistleblower: Hospital: x + 2 hours + 50 minutes. Now, this is just a realistic educated guess on how long Waylon spent in the hospital, but I believe he spent around 50 minutes before escaping.
Whistleblower: Recreation Area: Above time at night. Now we now it is pitch black and fog coated outside, meaning that x = night, unless the Underground Lab part took place in the afternoon right before night and it only took 2 hours and 50 minutes for it to become pitch black.
Whistleblower: Recreation Area : 3 hours and 3 minutes into night. Waylon walks around the Recreation Area for about 13 minutes.
Whistleblower: Prison: 3 hours and 13 minutes into night. It takes Waylon about 13 minutes to get from the Prison to Drying Ground.
Waylon then spends about 7 minutes in Drying Ground before falling into the Vocational Block. Spends time in there for 35 minutes, for his time from Dennis to killing Gluskin. That's 3 hours and 55 minutes, but I'm just going to round to 4 hours. But wait! Waylon is knocked out for 12 hours. 16 hours, plus the 7 additional minutes it takes to escape the asylum, and that's the morning. The sun goes down at about 7 PM and rises at 6 AM in Colorado's region. 11 hours. After jumping out the window in the Vocational Block, it's still dark outside, and around 13 minutes later, it's light.
But it's still midnight when Miles arrives to the asylum.
So, here's what I got.
Underground Lab (Whistleblower): 3 PM
Hospital: 5 PM
Recreation Area: 6: 30 PM.
Prison: Almost 7 PM.
Drying Ground: Around 7:07 PM
Vocational Block: 8 PM.
Gluskin drugs Waylon: 8:20 PM
Exit: 7:25 AM.
It's about 6 AM when Underground Lab (Outlast 1) begins, as you can see for a split second in the rigged elevator. On average, it takes about 4 hours for someone to complete Outlast, but remember that Miles was unconscious for who knows how long between Admin Block and Prison Block. Here's mine for Outlast:
Administrative Block: 8 PM.
Prison Block: 8:30 PM (excluding how long Miles was sedated)
Sewer: 9:10 AM
Male Ward: 9:30 AM
Female Ward: 11 AM
Return to Administrative Block: 12 AM
Underground Lab: 1 AM.
But of course, that just doesn't add up. The Underground Lab would have to take place at at least 7 AM, not 1 AM, for the timelines to make sense. So this either means Administrative Block begins at 2 AM (I could've said that in the first place, but this is more fun) or that Miles was sedated and lying in a Prison cell for 6 hours. We also don't know how long Miles was unconscious when Chris threw him out the window. I'd say Miles was unconscious for one hour in Admin Block, woke up to meet Martin, passed out for 2 more hours, then slept in the prison for 3 more hours.
Administrative Block: 8 PM.
Miles wakes after his meeting with Martin: 11 PM
Prison Block: 3:30 AM
Sewer: 2:20 AM
Male Ward: 3:30 AM
Courtyard: 4:15 AM
Female Ward: 4:30 AM
Return to Administrative Block: 5 AM
Underground Lab: 6:30 AM.
So there ya go, that's how I view the timeline. Want to share your own timelines? Go ahead, do it in the comments! By the way, DON'T say Hospital and Administrative Block takes place at the same time! People say this because they think the power-outage that frees Waylon in Hospital is caused by Father Martin when he turns off the generator in Admin. The slaughter began the moment the power went off in Hospital. Admin Block takes place a few hours after the slaughter.