Yes, the Wisconsin Department of Revenue requires you either file 1099 online, or you paper-file.
Yes, but you need to file 1099 directly with the State Department of Revenue.
You must file the 1099-MISC and 1099-R regardless of whether Wisconsin tax has been withheld, but the 1099-DIV or 1099-INT need to be filed only if there is state tax withholding.
Yes, the state of Wisconsin mandates you file Annual Reconciliation Form WT-7 when filing 1099 forms if there is state tax withholding.
Form WT-7 is used to report employers’ annual reconciliation of Wisconsin Income Tax withheld from wages. WT-7 needs to be filed only if forms 1099-MISC, 1099-R report withholding. The amounts reported on the WT-7 should match up with the taxes reported on these forms.
The filing due date for both is the last day of January.
The State of Wisconsin accepts both e-filing and paper filing.
The state of Wisconsin mandates electronic filing when submitting 10 or more wage statements (1099s). E-filing is preferred in general, but if you are submitting fewer than 10 1099s you may paper file.