Hmm... its the left that looks more 1920s brick bungalow-ish to me, and the right a later addition? One school of thought is that you shouldnt get overly matchy-matchy with trying to make an addition same color as the other part. They will never be mistaken for same original house, and it can look awkward to try. Let them be different, but they must work well together color-wise. I would make the section on the right a dark color, or at least a midtone (dark recedes visually, lights/whites come forward) and thus let attention focus more on the brick/ entry way portion. You could repeat the color you choose for the right side on the shutters on the left. Cant see what current shutter color is, possibly that would work for your paint color on the right? If you post a close up of the brick that could help narrow down color options.

I was considering painting the shutters black or ditching them completely since there aren't any on the addition..?? I never thought about going darker on the addition. That's a really great point!

What paint colors do you recommend? And should I get rid of the shutters?

Is this a single residence or two?

If it’s one residence, which door do the residents use the most? And which door do visitors use?

This will eventually be two residences but the goal is to make it feel like they belong together. Any advice would be appreciated. Thank you

Could you highlight the main front door and then totally redo the small porch and make that bigger and more inviting? Then you have two entrances - each one nice - but it could look less like two front doors.