So, I am getting back into riding steady for the first time in 15 years. Does STRAVA have a feature where you can track time progress for a specific ride over time? For instance, I want to see how much my time drops over the first month, 6 months, etc.

Yes. Ride your ride and make it a segment. You can make it private if you like.

Thanks for that tip. Will do. I pick my bikes up from the shop tomorrow and start riding to work.

Good decision

Here’s what it will look like:

Can I do this on the app, or do I have to get online? Or does this feature require a paid account with Summit I think it is.

Apparently you can only access this feature on the web and not the app.

I don't know if you can do it on the app. I only use the app when I go on a walk with my wife. Otherwise I use the web page. And no, it doesn't require the paid account. I've only ever had the free version.