IMO, when it comes to buying condos for personal use.....you either worry about the value/dollars, in which you shouldn't buy (for the reasons above), or you're sufficiently wealthy to not worry about the value, in which case you wouldn't be here asking for advice (and wouldn't care about increases in HOA costs or special assessments).

We have heard real estate investing is a great option to generate income and to become wealthy.  

@Nick Bleser In B&H the two biggest external risks are:(A) a decrease in demand and (B) a change in neighborhood desirabilityIn both cases, your revenue is threatened AND there's a potential need to increase expenditures - there isn't much you can do about it.Apply that to market cycles, and you're assuming risk if a cycle is likely to decrease rental demand ... because fewer people will want to culturally rent, because there will be more supply, or because there's a declining population IN THAT AREA.  

But as I first time investment I don't think $247/ month going into a $345,000 asset should be considered a money pit. as a beginner can that be looked at as a way of building wealth? I

I have come to the realization that real estate is a path to wealth I want to explore.  

In the 1950's the population was near 3,600,000 with it being close to 2,700,000.However, that past information and not necessarily indicative of what is in the future for Chicago.Per my research - median home sale price is $170,000.You should be able to find a home to cash-flow at that price point.I also heard that was a recent state income tax increase which made some wealthy individuals move away from the state.I believe Chicago provides more opportunities to find cash-flow positive properties.

Our general suspicion is that it's a standard relocation choice, but curious if we're off on the cultural waves.

So those will take a lot of risks could be very wealthy but they could also lose everything.

I'm looking for more of the operational efficiency and KPIs to be tracking as well as culture within the organization and processes and workflows. 

First read books starting with Richest Man In Babylon and The Wealthy Barber.