I might not have been super good at explaining!
Garmin segments are essentially a Strava segment knock off. There are headunit displays to show if I’m faster or slower than my personal best but as soon as you connect to Strava the assumption is you’re using Strava segments (which is a fairly safe assumption) but Strava doesn’t allow this without paying - which I don’t want to do for just a few segments I’m interested in.
So that I can see if I’m faster than last week I need to stick with Garmin segments, which isn’t the worst thing I’m never going to trouble the top 10 popular stuff I just want to try hard.
This then means I need to either manually download from Connect and up to Strava or was hoping for a tool to connect to Garmin that would push for me. Some sort of middle man. Which is what you suggested (big thanks for the idea 
) but I’m fully Garmin’d up with watches/headunits.