One solution is to leverage serial numbers (really lot numbers).

Each can have a 'best before date', and an 'end of life date' which can probably easily be shown alongside the product on each line.

You need to enable 'Track serial number on products' and 'Expiry date on serial numbers' under

Settings --> Configuration --> Warehouse

Each time you deliver goods, you assign each product that expires to a serial number. The serial number already shows up on the Delivery Order PDF so the other properties of the serial number should be available.

Haven't tried.

Yes, you can create a trigger or stored procedure in the database to do that.