What space is behind that bare left wall? I do not think you have enogh space to do a porch that will be in the right proportion to the house on that left side I am not sure of the prupose to that driveway connecting to the basket ball hoop can you not remove that then you could add the proper sized porch to connect to the side one . If the driveway cam from the road up front then you could eliminate this weird one I assume the other buildings are also yours maybe give us that info too.Even the window on the right is an odd size . Are you renovating the inside ? IMO if so then wait for the exterior fixes until the interior is done.

Very cute house. If you do black trim…. Will you also change the gutters to black as well? Just one of those… one thing leads to another type decisions …I’d think. How about the columns at the front porch…I’ve not seen many painted black ( but it could be cool). Totally not a design expert, but wondering if black windows would draw more attention to the non uniform placement… it’d be lovely if someone can help you design a porch 🤞. If not, i think a good landscape designer could do a plan to fill in and hide areas. Those bushes you have are pretty… maybe more? And layers?

Would need to see the interior floor plan to make appropriate suggestions for any kind of porch that wraps the house.

If you're doing a porch, get rid of the two porticos, which look like they were stuck onto the house at some point. Do some sort of overhang across the entire porch, if possible. Similar to these:

Front Facade and Yard with Brick-Paved Walkways · More Info

Modern Colonial Four-Square · More Info

That house looks like it's had a lot of changes over the years and not all for the better. I'd go to your historical society and/or town records office to see if you can find old pictures with some idea of what it once looked like.