Since the STS Edition2 introduction, all vending systems are tested for TID rollover compliance. This has been in place since 2017.
The certificate of the vending system or meter will state the edition that they are certified to. Although older meters will only be certified to Edition1, they must still support the TID rollover functionality since this has been part of the IEC62055-41 specification since its initial publication. The security module type and serial number should be communicated to the HSM supplier to check compatibility with STS Edition2.
This depends on your contracts with meter and vending system manufacturers.
Yes, it will.
Yes, it will.
Yes, it would. It must support both base dates, in fact it supports 1993, 2014, and 2035 base dates.