Because little Johnny's Mommy wasn't too pleased when showed what the "nice kid with a backpack" gave him for selling him his "toy" and found out it was worth a whole lot more than a "handful of jelly beans".... 

That’s great advice Taz, I’m currently working on saving enough money to get started, house hacking is hard for me at the moment because I just bought a house 2 years ago, I would have to sell my house(which is in a great neighborhood great location) and use that money to fund the duplex which isn’t totally out of the question, I would like to keep the house if possible but also would like to get real estate investing more.

.: I haven't passed this past legal review so for what its worth: Part of my standard requirements for everyone include income is at least 3X rent, minimum credit score, say 640, Clean record and no evictions as well as deposit is paid in full at signing of lease and 1st month rent is paid in full prior to handing over the keys.

You can also look into building a rental portfolio which is a little less hands off compared to flipping.

Nd what housing is currently attracting the highest CoC and total returns potential - studio - 1bd, 2 - 4bd, or 5+bd?  

I am guessing his hands are tied as Norada is simply the marketing company and I am guessing no operational control of Wagner.

I took the next 5 months to tackle everything myself spending approximately 17k in supplies and tools + paying a plumber and roofer 4k total to fix those issues.

I'm so glad you brought up trash, totally slipped my mind in my eval.

I'll add on to what the other Ben said and mention that there are exceptions based on the # of days that you rent out your home to where the income/expenses are excludable (being lesser of 14 days or 10% of total usage if under 140 personal use days).

Hey @Mike Nelson, never assume anything about STR rules and regs.Here is the STR rules for Oak Park - https://codelibrary.amlegal.com/codes/oakparkil/latest/oakpa...I would call the city and make sure it is legal for a specific property.Now regarding the famous person angle, sure it can add value to the property or as a STR, but for STR use, I would think you would need it to be in original condition with a lot of the furniture and knick-knacks that were owned by the famous person along with a bunch of photos etc featuring the famous person.If you buy a place that has been totally redone but was owned by someone famous but has no features or things that were theirs, then I don't see it being a draw.