I actually really enjoy property management and was a property manager for over 100 units for 4 years with a big corporate company at one point.

I enjoy learning in a structured environment and also want to "rebrand" myself away from being a CPA to more of a businessman.

At least it is for me.I am a firm believer in outsourcing the things you don't like to do or aren't good at and focusing on the things you do enjoy. 

They are easy to manage so far, so I’m enjoying the cash flow.

Cited in IRS Chief Counsel Advice 201640014 it is noted that "1402a13 was intended to apply to those who 'merely invested' rather than those who actively participate" - this is also based on the above caseCited in the counsel memo above - Riether 919F Supp 2d 1140 "Limited partners are those who lack management powers but enjoy immunity from liability and debts of the partnership".As noted - OP still has a steep hill to climb.

If the PM doesn't charge a late fee until the 5th, how will that impact your ability to pay bills, build wealth, or enjoy your children?

For us, this is a home we are using as a family gathering place in addition to a STR so the extra work is worth it to me and I really enjoy talking to people.

I chose Airbnb as we do that when we travel and really enjoy it. 

My background is in healthcare but I actually have enjoyed using my creativity for marketing lately, hopefully that will help too!

Hello Shawn,I would first off like to say that we appreciate your business and have enjoyed being able to help you out on your various projects.