Wow! This is amazing. Manually setting the item with sendCommand(99.0) stores and restores the value, but it gets absolutely ignored during startup and the rule (which should only trigger on 4.0) triggers anyway. 
Here is the log during startup. I added some logging rules:
2020-08-26 01:31:44.101 [INFO ] [ui.habmin.internal.servlet.HABminApp] - Started HABmin servlet at /habmin
2020-08-26 01:31:44.813 [INFO ] [openhab.ui.paper.internal.PaperUIApp] - Started Paper UI at /paperui
2020-08-26 01:31:46.174 [INFO ] [e.smarthome.model.script.Alarm-Rules] - Alarm is disabled
2020-08-26 01:31:46.178 [INFO ] [se.smarthome.model.script.REMOTE-UPD] - ++++++++++ Garage door button was pressed ++++++++++
2020-08-26 01:31:46.183 [INFO ] [ipse.smarthome.model.script.TEST-UPD] - ********* triggeringItem: From state 99.0 to state 99.0
2020-08-26 01:31:46.176 [INFO ] [ipse.smarthome.model.script.TEST-CHG] - ********* Item Changed: Prev state NULL changed to 99.0
2020-08-26 01:31:46.200 [INFO ] [ipse.smarthome.model.script.TEST-UPD] - ********* newState: 99.0
Edit: Well okay, maybe because I change the item value in OH but it gets re-initialized from the open zwave stack. It is a zwave remote. So the hack won’t work anyway.