We are based in Alaska and have 2 primary airlines: Delta and Alaska.

It's also worth mentioning that I already have a good relationship with a wholesaler in town who knows other good contacts, and I am able to use some of these contacts as good resources for general knowledge and learning how it all works.I recently had to close my business of 9 years, and so instead of getting a W2 job or start some other "normal" business, I'd much rather prefer to have house flipping be my primary source of income. 

This way you can fix up your primary residence to build equity and also add a cash flowing rental.

I'm 30 with a family of four, just bought my first primary home this year.

Neither for that matter will a DSCR loan when/if you go to get a full primary home loan for example for the same reasons.

Assuming the insurance premiums don’t significantly impact my cash flow (which is one of my primary goals), how do you assess the risk of taking out a loan under my personal name versus opting for a commercial loan that requires a larger down payment and comes with a higher interest rate?

Those were my primary reasons. 

You can acquire a primary residence as low as 3.5% FHA or 3%-5% for conventional.

Also, I payed my mom’s mortgage on her primary which I can rent here in San Diego which would help with the mortgage but I rather not use that in the calculations to avoid over leveraging myself.

In many cases it is fully legal so long as it is your primary home and you occupy one of the units but definitely make sure you're in compliance before you move forward.