I have been researching and helping others research for over 10 years. I was a member of the original RAOGK from about 2006 until it was disbanded, and since that time have volunteered my time on other genealogy help sites. I have a deep background of researching in the Dane County area. See below for a brief description of things I can help you with:
Any time of the year: Can look up obituaries in Dane and Milwaukee county newspapers that I have online access to, 1920-present (earlier years have less chance of finding an obit).
Certain times per year (since I live in Georgia, but make frequent trips back to Wisconsin): Can visit the Wisconsin Historical Society and obtain copies of birth, marriage and death records from the pre-1907 records which are stored there on microfilm. Can also look up probate records for DANE COUNTY ONLY.
You would just reimburse for cost of paper copies. This can be discussed at the time of your inquiry.
If making a pre-1907 record request, please look through the Wisconsin Pre-1907 Vital Records Index (http://www.wisconsinhistory.org/Content.aspx?dsNav=N:1161) first to determine that there is actually a record for the person you are looking for. It is important to note that registered birth, marriage, and death records were not required until late 1907, so even if your relative had a vital event occur in Wisconsin, there may not actually be a record of it at the state level. If that is the case I'd recommend looking for church records.