Question   In your opinion can we use the standard server for a 2,000 member site and expect it to run okay? (2 pages and 2 sets of AR's)

A. A member cannot belong to more than 1 membership. Instead, you can setup so each membership has different content.
Then make the membership that the member upgrades to include all the content from the member's original membership.
You can do this by setting up content groups and attaching them to content.

A. Because you are selling multiple memberships you would need the $600 Tool Truck.

A. The easiest way, if possible, is in the database to temporarily make any suspended members active.  Then make all the members in the membership suspended.  Then from members delete to delete all suspended members.  Then suspend the members that were previously suspended.

A. Yes

A. It can, but it doesn't have to.  You can have multiple payment buttons on the same page.