Hi.
You can deploy a migration from RIPv1 to RIPv2 easily by configuring all the routers to send and receive v1 and v2 RIP packets and then change to version 2 only. This way I believe you won't have problems.
By default a router running RIPv1 only sends RIPv1 packets, but listens to and understands RIPv2 packets also. So maybe you don't even need to do what I suggested above.
Regarding the auto-summary issues you won't feel the difference after the migration because RIPv1 as you know is classfull! RIPv2 has auto-summary enabled by default, so if you want you have to disable it manually.
Regards,
NM