6 weeks in the north first time there

I think it helps to share some things about yourself and why you chose Milan. Obviously Milan has many fans, but we all go to Italy for different reasons so might have different ideas about where to stay. Have you been before? Do you prefer cities in general? Where else will you go on this trip?
For more scenic, nature focused places like the lakes, I have a strong bias -- I just think waking up there is a totally different experience. Knowing your aims and such helps others keep that in mind and not just say what they prefer--which I fully realize is what I have done in this post (trying to make my point)!

Here is a great place to say in Turin, assuming it's the right size for you. Great location close to a huge market and away from the city center (but still easy to get there). We spent about a week in Turin and LOVED it. Cinema Museum with rooftop viewing deck. Great old tram cars. Original Eataly. Car museum and old Fiat factory with rooftop test track.
https://www.airbnb.com/rooms/7251319?source_impression_id=p3_1727452077_P3GYOl2ywqbpuy3e

I’m another non-fan of Milan. You could make some great trips from Torino to Alba, the Barolo/Barbaresco/Asti wine region and the Val d’Aosta area where you could take the Skyway Monte Bianco to the top of the Italian Alps. The Piedmont area is under-touristed and a great place to visit. I would also consider Lake Como a must see!

I think you should consider spending a few nights in three locations - Torino, the Piedmont and Lake Como. There’s too much to savor than just making a day trip.

We stayed in a great Agriturismo in Barbaresco and i’d highly recommend staying at the Agriturismo Tre Stelle.

Thanks for the replies. We looked at Milan because it was centrally located. The driver of this trip was to relax and enjoy Italy. We have never been north of Venice so we thought that this would be a great opportunity to live like a native. On the flip side, we wanted to see some of the sites with a two to three day and out experience.
We have narrowed down our list to Como, Bergamo, Tourino, then Genoa, Cinque Terra Santa Margherita, then settling in Bologna for a few weeks and traveling around that area. We are trying to strike a balance between being occupied but not over stressing about jamming in too much if that makes sense.

I guess you can only look at pics and read up on Milan to decide if it looks appealing to you. I would lean toward Torino for the reasons expressed above, even if I had to split a two week period into a week there and a week on a lake.

We have narrowed down our list to Como, Bergamo, Tourino, then Genoa,
Cinque Terra Santa Margherita, then settling in Bologna for a few
weeks and traveling around that area.

I think Bologna makes a great base because there are so many day trips in E-R along the train line, but Bologna still seems to have that certain something.
Are you looking for one northern base, one coastal base, and then wrapping up in Bologna?

You have made a very good plan. I can't improve on it. Having returned just last week from Bologna I concur. Bologna has that certain something. Avoid Milan.