Yes.
1500-1500, yes
YES
yes, same bolt pattern
No.No.
Yes
Yes
No, they will not clear the brake calipers.
If the 1999 is a four wheel drive, yes. If two wheel drive, no. The rims will not sit all the way on the hub.
5 on 5.5
Yes
1991-2004 Chrysler 300M rims should fit the 2001-2006 Caravan
Yes