.- The best cash flow in this market is achieved via STR, MTR, or rent by room. 

My tenant moved out a couple of days ago, and when I walked through the unit, I discovered that he had removed the curtain and curtain rod, detached the room air conditioner, and caused significant scratches on the hardwood floor from the metal bed frame legs.

I think the opposite is more achievable.

Our unique partnership model ensured that both Erika Gilbert and Partner Driven were financially aligned to achieve maximum returns on the sale.

Work at a bank or hard money firm that makes loans on the types of deals you are interested in.Real estate investing has lots of different facets within it, so getting specific will help you achieve your goals.

However, $750/mo rent for a 2BR unit is exceptionally cheap, so it could be in a bad or depressed area, so that price may not be so cheap.

@Tim Phillips I would recommend looking somewhere that's affordable, in a landlord friendly market and of course that meets the goals you're looking to achieve.

Making the basement a legal unit is costly but can be done as an ADU depending on your exact location (ADU zone maps are on City of Chicago site).

Glad this post of yours was restored Patricia, i like the topic, thanks for posting.My rates have always fluctuated too however it hasn't hurt my ranking with VRBO.Personally, i noticed for my listing, the ranking improved once i achieved greater than 50+ reviews and once my listing matured (listing age greater then 4 yrs).

Those that claim to cashflow well are either a) full of it or b) old and in a class C area where your probability of being able to achieve those cashflows are low.