Filters are and have been very confusing here for many so you're not alone. Since you seem open to working on getting this to work, I'll offer up some suggestions from one who has many analog systems programmed in both my SDS100 & SDS200.
Chicago has 450 & 460 Mhz. systems in use, and I monitor by local suburbs in the 470 Mhz. band. I don't have any suggested remedies on VHF-Lo but maybe these will help. First...the filters. You might know this already, but when you adjust filters they can be done by site/department or globally (which effects the entire scanner). If you're making an adjustment at the Department level, it will override the Global setting. If you set the Department to Global, only then will it accept the Global setting.
For me personally, to monitor analog systems I set my Modulation to FM from Auto (which is the default setting). I don't know the technical reason why this works, but it does. The same x36hp scanners that were receiving analog fairly well, my SDS scanners now exceed the reception, so yes their is hope. If this setting is used, you will notice the audio is lower on your analog channels. Simple solution...Volume Offset +2 or +3 and you should see an improvement.
As I read, you've experimented with the filters without much luck. I'd recommend Wide Invert or Wide Normal settings. Many of us here with challenging environments seem to have better luck using them, once again I don't know the technical reason for it. First try it at Department/Site level, and if you find these settings work best, change the setting to Global, and in the scanner menu change the Global Setting to whichever works best. Experimentation is the only way to go on this.
I would repeat this on the simulcast system that seems to be sketchy. For that, you'll have to drill down to the Site level. And...as you've been doing, once you're done, Read the Scanner into Sentinel and save it.