These two items can result in extremely poor returns if the purchase happens to coincide with a period of modest or worse appreciation.  

Realize cap expense items are very costly.  

A household with more than $1MM in net worth excluding their personal residenceThere are some other options and more details, but if you can check either of the items above, you are safe to call yourself an accredited investor.The more complicated designation is the Sophisticated Investor.

@Emma PowlinAny contractor can give estimates for remodeling, but does the contractor know/understand the unique paperwork, compensation structure, draw request process, change order process, allowable items, required items, etc.? 

Would condos be a better option to avoid high ticket maintenance items like the roof and garages, landscaping etc?

I used to work as a rent collector and handling complaints for a guy who owned bunch of multi units from Class A to C in Los Angeles to Santa Monica.  

Lots of differences you are seeing about Chicago compared to elsewhere and I will share an ebook we created to help out of state investors get some insight on huge items we see a lot of people miss when coming into this market.  

As you grow larger than you can consider these other items and utilize CPA and Atty who are actual real estate investors and work with real estate investors.

As others have said, the process is not rocket science, but without extra personnel or way more time than I have there’s no way I’m texting cleaners on ever-changing schedules.TurnoverBnB’s pretty good at what it does and the I’ve found the inventory management side of it be increasingly valuable, but the software is pretty bad/buggy and yes some cleaners will just refuse to use it or check off all items in 30 seconds as they head out the door, which defeats the purpose of a checklist. 

Due to item 1, adding an ADU can require years to start achieving any return (once the accumulated cash flow recovers the initial negative position).4) Adding an ADU is a slow process.