Hi @kamotekid :
I've made a test for your reference:
1\My table:

2\My Flow:

My Expression:
@and(
less(formatDateTime(Concat(split(item()?['Proprsed Start Date'], ' ')[2], '-', split(replace(replace(replace(replace(replace(replace(replace(replace(replace(replace(replace(replace(item()?['Proprsed Start Date'], 'Jan', '1'), 'Mar', '2'), 'Feb', '3'), 'Apr', '4'), 'May', '5'), 'Jun', '6'), 'Jul', '7'), 'Aug', '8'), 'Sep', '9'), 'Oct', '10'), 'Nov', '11'), 'Dec', '12'), ' ')[1], '-', split(item()?['Proprsed Start Date'], ' ')[0]), 'yyyy/MM/dd'), formatDateTime(utcNow(), 'yyyy/MM/dd')),
startsWith(item()?['Title'], 'Approved'),
greater(formatDateTime(Concat(split(item()?['Proprsed End Date'], ' ')[2], '-', split(replace(replace(replace(replace(replace(replace(replace(replace(replace(replace(replace(replace(item()?['Proprsed End Date'], 'Jan', '1'), 'Mar', '2'), 'Feb', '3'), 'Apr', '4'), 'May', '5'), 'Jun', '6'), 'Jul', '7'), 'Aug', '8'), 'Sep', '9'), 'Oct', '10'), 'Nov', '11'), 'Dec', '12'), ' ')[1], '-', split(item()?['Proprsed End Date'], ' ')[0]), 'yyyy/MM/dd'), formatDateTime(utcNow(), 'yyyy/MM/dd'))
)
The Result:

Best Regards,
Bof