I only have "Copy B for recipient" from fund company for 1099-Div and 1099-B, is it ok to make copy and send that in if I don't have any other copies, such as a Copy 2? (this is for State of Illinois which asks for copies of 1099 to be stapled to return)

Not sure why I received 1099-R in 3 copies from Vanguard (Copy B for federal return, Copy C for my records, Copy 2 for State, City of Local), whereas 1099-Div and 1099-B only have been provided as "Copy B for Recipient"

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I only have "Copy B for recipient" from fund company for 1099-Div and 1099-B, is it ok to make copy and send that in if I don't have any other copies, such as a Copy 2? (this is for State of Illinois which asks for copies of 1099 to be stapled to return)

Sure, it is OK to copy the information and send it in. You always need to keep one copy for your own records.

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I only have "Copy B for recipient" from fund company for 1099-Div and 1099-B, is it ok to make copy and send that in if I don't have any other copies, such as a Copy 2? (this is for State of Illinois which asks for copies of 1099 to be stapled to return)

Only those forms showing tax withheld for the tax agency should be included with your mailing..

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