Out of curiosity I tried this with my two radios on the Outagamie/Winnebago TRS.
(I'm way up here in Waupaca county but occasionally visit Milwaukee and have listened to OASIS on my PRO106. I think the Outagamie/Winnebago system will be similar as it is also simulcast.)
When programmed using WIN500 and simply importing the system my radios exhibit the exact same behavior. I think this is because WIN500 defaults to 370, 450, 520, 610 and 680 for the S meter settings. That works fine for the PRO106, but the WS1040 needs much lower settings to give anything meaningful for the S meter. I use 190, 230, 260, 290 and 320. Also, I have changed several settings to get similar P25 decode between the WS1040 and the PRO106. If you are curious I can send screenshots of my WIN500 "Extended Settings" tab for each radio, but your mileage may definitely vary there. Since you said you manually programmed them both I would start with changing the S meter settings in the "Expert Settings" menu in the radio and arrow down to "RSSI Sig Cal" and change them to the numbers I gave. That should at least get you the signal bars on the 1040.