Buying used 991 should I wait for 2020 model to come out?
Apple has a monopoly on my phone choices...I am a slave to their upgrades. PLEASE dont tell me that they have a hand in my decision on which Porsche to buy! 
Seriously, the differences between the 991 and the 992 are largely tech (ie the same updates to the Cayenne and Panamara) and esthetics. The 991 was the biggest change in the platform in years. The PCM is circa 2012 though, so there is that...you can either crack it open and give it new life with a Carplay update, or now there are great options for complete integration with the car and a new aftermarket head unit.
Items like car data, rear view cams, sat antenna, and even the cluster functions (except radio and nav selections) all function as before. The replacement brackets are pretty cool too, and we are talking plug and play with whichever stereo system that you have - standard, Bose, or Burmester. Suncoast sells a swap out kit that is virtually plug and play - I have a 2014 Turbo S Cab and I am swapping out the head unit. I had thought initially about the CarPlay system but the deck itself its pretty dated. Im opting for The ILX - 107 Alpine Unit.
The nice part about the complete swap is that its reversible.

Seriously, the differences between the 991 and the 992 are largely tech (ie the same updates to the Cayenne and Panamara) and esthetics. The 991 was the biggest change in the platform in years. The PCM is circa 2012 though, so there is that...you can either crack it open and give it new life with a Carplay update, or now there are great options for complete integration with the car and a new aftermarket head unit.
Items like car data, rear view cams, sat antenna, and even the cluster functions (except radio and nav selections) all function as before. The replacement brackets are pretty cool too, and we are talking plug and play with whichever stereo system that you have - standard, Bose, or Burmester. Suncoast sells a swap out kit that is virtually plug and play - I have a 2014 Turbo S Cab and I am swapping out the head unit. I had thought initially about the CarPlay system but the deck itself its pretty dated. Im opting for The ILX - 107 Alpine Unit.
The nice part about the complete swap is that its reversible.
If you look on car gurus depreciation curve the 2014 991 has actually started to appreciate in the past 4 months - an interesting trend
The bottom line is if you buy a new 992 you are going to take a significant loss over the first 3 years of ownership
If you buy a used CPO 991 from 2014 - 2016 most of the depreciation is already out of the vehicle
The question is if the trade off on having the newest technology and apple car play features and the like is worth the additional cost
For myself the biggest advantage of Porsche is the way they hold their value - my 997 Turbo has appreciated slightly a little bit every year for the last 3 years after it hit the bottom - I just bought a 2014 991 Turbo S and expect that could depreciate a bit more but not much more - personally I would never consider to but any of these cars new and take such a loss - to each his / her own
The bottom line is if you buy a new 992 you are going to take a significant loss over the first 3 years of ownership
If you buy a used CPO 991 from 2014 - 2016 most of the depreciation is already out of the vehicle
The question is if the trade off on having the newest technology and apple car play features and the like is worth the additional cost
For myself the biggest advantage of Porsche is the way they hold their value - my 997 Turbo has appreciated slightly a little bit every year for the last 3 years after it hit the bottom - I just bought a 2014 991 Turbo S and expect that could depreciate a bit more but not much more - personally I would never consider to but any of these cars new and take such a loss - to each his / her own
Apple has a monopoly on my phone choices...I am a slave to their upgrades. PLEASE dont tell me that they have a hand in my decision on which Porsche to buy! 
Seriously, the differences between the 991 and the 992 are largely tech (ie the same updates to the Cayenne and Panamara) and esthetics. The 991 was the biggest change in the platform in years. The PCM is circa 2012 though, so there is that...you can either crack it open and give it new life with a Carplay update, or now there are great options for complete integration with the car and a new aftermarket head unit.
Items like car data, rear view cams, sat antenna, and even the cluster functions (except radio and nav selections) all function as before. The replacement brackets are pretty cool too, and we are talking plug and play with whichever stereo system that you have - standard, Bose, or Burmester. Suncoast sells a swap out kit that is virtually plug and play - I have a 2014 Turbo S Cab and I am swapping out the head unit. I had thought initially about the CarPlay system but the deck itself its pretty dated. Im opting for The ILX - 107 Alpine Unit.
The nice part about the complete swap is that its reversible.

Seriously, the differences between the 991 and the 992 are largely tech (ie the same updates to the Cayenne and Panamara) and esthetics. The 991 was the biggest change in the platform in years. The PCM is circa 2012 though, so there is that...you can either crack it open and give it new life with a Carplay update, or now there are great options for complete integration with the car and a new aftermarket head unit.
Items like car data, rear view cams, sat antenna, and even the cluster functions (except radio and nav selections) all function as before. The replacement brackets are pretty cool too, and we are talking plug and play with whichever stereo system that you have - standard, Bose, or Burmester. Suncoast sells a swap out kit that is virtually plug and play - I have a 2014 Turbo S Cab and I am swapping out the head unit. I had thought initially about the CarPlay system but the deck itself its pretty dated. Im opting for The ILX - 107 Alpine Unit.
The nice part about the complete swap is that its reversible.
I concur with your thoughts - a lot cheaper to buy a new head unit than spend $200,000 plus on a new 992 turbo when they finally come out - only to have then depreciate down to $120,000 like all other turbos did
Honestly though I think the majority of new Porsche sales are lease cars
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