However, I know this will be very difficult to pull off and is a high risk, especially since I'm already using a lot of time for my full time job and building up my insurance agency on the side after work.

So, its difficult to handle sudden changes in their expenses.

Something that makes my situation a bit more difficult is that I have a job in Hawaii (6 hour time difference from EST. right now).

It may be more difficult if your mother doesn't help you.

We do have a $25/hr charge for really difficult situations... in 5 years we only charged it during the recovery of hurricane Ian.

It WILL make it more expensive, more limited, and more difficult for buyers in general. 

As for being named individually, while the standards will vary it is generally very difficult to pierce the corporate veil and comingling the funds is the most common culprit.

Sure you can get relatively cheap properties in Toledo and Cleveland, but at today's interest rates they'll be difficult to cash flow despite what your analysis shows on paper.

Quote from @Candi Kham: Section 8 has a lot of good and bad, but it's difficult to make a wise decision when you don't know all the ins and outs.

Can you afford to live in Hawaii and self-manage, or do you have to hire a property manager when the good ones are extremely difficult to find?