I am a pretty meticulous person so I actually don't mind the task I just don't understand it yet. 

This would allow me to buy the houses for cash, below market rate, fix them for instant increase in equity, and then rent them for monthly income (or to use the income for additional homes if it is not needed for my travel adventures). 

You may work as a w-2 employee and I believe you can also under a resident managment agreement and do property managment tasks in Ohio but the rules vary from state to state.

I would contractually agree with each of my sub-contracted property managers to a list of on-going operational tasks I would solely be responsible for doing, to prove I am continuously and actively participating in the management of my properties. 

One of their tasks is to assist people developing ADU's.

I now have the task of selling their amazing condo, it's in one of the best neighborhoods in Chicago, there is low low volume in the area and it has a garage parking spot with the unit (anyone living in Chicago knows how great that is especially in the winter), the condo can be rented out, the place should sell itself.

The creative developer will be tasked with displaying their talents on all four floors.

The book by 4 Hour work week by Tim Ferris has been my inspiration and found that being able to focus on one task at a time would be most productive in my case.

Closing on two units simultaneously was a deliberate part of my strategy, but there are pro’s and con’s to this approach:Pro’s- Each step in the process I’ve completed x2 at a time, saves a ton of time- As a new investor, my growth and learning curve seems to be accelerated as I do everything twice- Comparative analysis, I can measure experience on one property against the other - Working with one lender, settlement on both properties on one date- I double up the items on my task lists, which means if I make a mistake on one, I correct it on the other- Twice the investment means twice the income Con’s- Twice the amount of physical work, driving, cleanup and maintenance- Twice the risk exposure on the investment, I have two applications pending on one while the other I’ve decided to lower the rent- While my interest rates were very competitive, as a new investor I had to put 25% down on both propertiesSo far in the process, although I put more money down up front, it seems like closing on two units simultaneously has been advantageous to my cash flow strategy.

I started doing things like building a clothing business, being an adventure guide, photographer and most important working in my parents restaurant.