Can I wake up in Bologna and still make my Milan early afternoon flight ?

A bit over 2 1/2 hours by fast train with one change (I would not drive) Bologna Centrale to Malpensa T2. Can it be done, yes. Would i be comfortable- maybe not. Assuming 3 hours before departure at airport pretty early departure Bologna. Things do happen.

The only problem is if there is some issue with the rail line on the morning of the 10/17. If there is any kind of delay, you are out of luck getting to Malpensa by 11 am. Safest is to go the evening before and stay at an airport hotel.

A strike will be announced well in advance, so you can plan for that. But unforeseen delays include: accident on the line, electrical power outage, equipment problem, crew problem.

I agree with the above posters.

It boils down to your acceptable level of risk.

Nope, it would stress me out but everyone is different.

Can you? Absolutely. Its physically possible to either drive or take a train (actually trains- a connection would be required) as long as you leave early enough. Like between 06:30 and 07:30. The train is faster than driving, and you dont need to futz around with gas fill ups and drop offs. But as already described, there is a non zero risk that something disrupts the train(s) and leaves insufficient time for a plan B. So should you? How lucky do you feel?

I wouldn’t risk it

Consider staying in Stresa in Lake Maggiore
Closer to Malpensa than Milan, direct airport bus
https://www.safduemila.com/linee/alibus-malpensa-lago-maggiore/

New proposal:
Train to Modena on 10/16
Spend day in Modena and stay overnight
Car service to MXP the next morning. It is about a 2 hour drive.