But that person would have to be on the loan in order for the experience to count.I usually encourage partnering with an experienced investor for the first few deals in order to learn and reduce your risk by minimizing "newbie" mistakes. 

My question is once the year is over, assuming that I purchased the property under market with minimal repairs and I am able to pull out the equity.

I am glad to be in Vegas where these changes are minimalized or not a factor at all like the S.A.L.T. cap.

I've been reading everything I can find and listening to the podcast, but I still have a question.If I go FHA at 3.5% down to minimize out of pocket cost up front, how do I have the equity to refinance into a conventional in only a year or two?

Repaving made all the difference in the world but the kicker for you will be to get the other owners to pitch in for their fair share, since you're the end unit. 

If they want it I suggest they pitch in effort or material....

That way your cleaning and restocking expenses will be minimized.

I’m trying to minimize any future issues.

Therefore, I think we should also plan to do a Roth Conversion Ladder on $19,049 (less than the $19,050 to still be in the 0% income and capital gains tax bracket) to minimize taxes paid on some of the 401K money.

I’ve been searching for a 4 unit turn key house hack in Chicago in my price range since September and haven’t found not one that cash flows or the ones that do flow is so minimal it’s not worth it.