Session watcher not respecting reticulate delayed load, and other issues

There seems to be some weirdness happening with reticulate when working with the VSCode-R extension. It looks like VSCode-R is evaluating the reticulate/Python code in a different way than the standard R GUI console. The obvious example when using the delay_load flag when importing modules:

standard R GUI Console

library(reticulate)
start = Sys.time()
re <- import("re", delay_load = TRUE)
end = Sys.time()
end - start
#> Time difference of 0.01495004 secs
re
#> <pointer: 0x0>  # the module has not been loaded yet because delay_load = TRUE

start = Sys.time()
re$match  # trigger loading of module
#> <function match at 0x000002EA31AE8B80>
end = Sys.time()
end - start
#> Time difference of 12.2005 secs

VSCode-R Console

library(reticulate)
start = Sys.time()
re <- import("re", delay_load = TRUE)
end = Sys.time()
end - start
#> Time difference of 12.08285 secs
re
#> Module(re)  # module has been loaded

start = Sys.time()
re$match  # trigger loading of module
#> <function match at 0x000001C7AD980AF0>
end = Sys.time()
end - start
#> Time difference of 0.03116894 secs  # fast because module was already loaded

I have also been encountering cases where reticulate will throw Python errors in VSCode but not in the R GUI, and will continuously re-throw the error with every new command. However, I do not yet have a reprex for this (it most commonly occurs with the arcpy module, which is not available unless you have an ArcGIS Pro license). I'll post again here if I can reproduce the issue with a publicly-available module.