Seems like updating to iOS 13.7 fixes this. I was never able to get Xcode 11 to work with 13.6.1.
oalejel
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I figured that I could look into the console (specifically, the macOS console app that displays my connected iPhone's logs), and I found a message describing a "budget" allocated to the timeline being decremented. I'm not sure how to interpret the budget object this log describes, but I think you might get an idea of how often the budget is decremented.
default 22:57:35.720663-0400 dasd Decremented widget refresh budget for <private> by 0.250000, budget is now <_DASWidgetBudget <redacted by me>::medium::1160724381304447037::{329.0-155.0}::21.6: 56.50/ 75.00>