Definitely need some additional details here.
It appears that both Madison, as well as Cottage Grove, have talkgroups on the same system:
DaneCom Trunking System Profile
www.radioreference.com
However, the Madison TGIDs are in a department labeled as ISSI talkgroups, presumably referring to their being patched from a different system. I see a separate system actually listed under Madison on the county's database
page.
Madison Public Safety Trunking System Profile
www.radioreference.com
Looking at the site details for Madison's system, the
page does not list a license, so the map would not show locations if the site is actually simulcast. However, in checking the site frequencies with licenses in your county, I find this license:
FCC Callsign WNXW548 (MADISON, CITY OF)
www.radioreference.com
The map for that license appears to show it is actually simulcast:
View attachment 112181
You say that you have no trouble listening to Madison.
While it does appear to be simulcast, the tower site indicated by the
4 on the map is relatively close to you in Cottage Grove. Simulcast issues are extremely location specific. It's possible that you may be getting a strong enough signal from that one tower to drown out the out of sync signals from the others, and thus you can hear Madison.
For Cottage Grove, on the Dane County system, you have a much different situation. Look at the map for the Dane County system's simulcast site:
View attachment 112182
Compared to Madison's system, the Dane system has a literal forest of tower locations, at varying distances from you. That can hammer your scanner with conflicting out of sync signals, making it impossible for your 436HP to correctly decode the control channel & allow you to listen.
Since the screenshot of the Favorites list you provided only shows a limited Dane County system, with only the Cottage Grove talkgroups. you apparently using a separate list for Madison/ Nothing wrong with doing that, but it does make it harder to see what changes might be helpful to make.
As
Jim has already suggested, attach your list for Cottage Grove. I would also suggest that you provide the list that includes Madison. You'll have to export them individually, you can select both of them at the same time, them 'send' both to the same compressed file which can then be attached to a post.
More details on Simulcast can be found in the Wiki:
Simulcast digital distortion - The RadioReference Wiki