Help - MMI Upgrade - Risky or Harmless?

Hi there!

I recently purchased a 2016 A5 Audi which comes with a retro CD player. Unfortunately I binned all my CDs about 10 years ago so I am looking to upgrade the MMI to something like an Apple Carplay but I have some concerns I am hoping some wise petrol heads can help me with please!

1. How risky is this to do? (Full disclosure, I have no desire to do this myself and would be using a specialist company to do this for me). Could it effect the actual MMI itself?

2. When I upgrade, do I lose all the ability to see the current items on the MMI like vehicle information 

3. Once the carplay is installed, is it all ongoing upgrades remotely?

4. Would this effect my ability to sell the vehicle in future?

Ps. I intend on telling my insurance company too

thanks!