If you have multifamily commercial loans, you will likely have to repay the loan in the near future instead of having the payments applied to the end of the loan. 

Having a vision for future projects like the ones you mentioned are great, but learning the ABCs of RE with a small investment (initial down payment - since you only need 3.5%-5% down on a primary) is the best way to sharpen your skills.

This was a brilliant idea, I didnt get to try it, but certainly will in the future. 

With future income you pay off that loan as well.

Currently I'm looking for some kind of methodology, software or app, that I can use to manage the properties, which will allow for another family member to step in to my role relatively seamlessly if I were to pass in the future.

Pay your vehicle loan, credit cards, etc because in 12 months all of the accounts you pay out of a business checking account will be omitted from your DTI in the future. 

If rates go down in the future, we likely will have another run up in prices, so it might be worth it to Airbnb while waiting that out for a couple of years. 

@Tanner KingWhen I analyze a house hack deal, I focus on metrics like GRM, Cap Rate, Cash Flow, House Hack Savings, and Future Rent Potential.

These connections can provide insight into reasonable pricing and offer trustworthy referrals for future work.

Looking forward to building a better financial future.