Is it remaining a multi-family or are you turning it back into a single-family? It looks like the front porch was enclosed at some point and the stonework would be supports for columns.

It would look fabulous with the front porch opened up again, although if it's going to remain multi-family, I imagine you would be losing some interior rooms that might still be needed.

I would put trim back to reference the columns:

Love palimpsest mock up of the columns. Improves the front a whole lot and it makes sense of the brick work.

It's a rental. Fix things that are broken, clean things that are dirty, and collect the rent when it's due.

I did the same thing, though mine was side by side. I'd still give you the same advice. When we moved out the extra rent paid our new mortgage.

I'd get rid of the stone and re-side the front of the house. There's a good chance that the wood behind it is rotting, or will in the future. Don't enhance the mess, remove it...

These porches were often enclosed where I lived, but the more successful in-fills windowed in almost the entire area between the columns to maintain the proportions:

Wider windows for sure. Am wondering how replacing the horizontal siding on the dormer with board and batten to match the lower front would look? The dormer is pretty horizontal in character and board and batten might counteract that.