The skill comes in sourcing deals that arent only on the MLS.

Parking will likely be your biggest hurdle.

In our market, there isn't much data outside of the census (I've checked Costar, CBRE, etc) do you know of any other sources i could use to back-up that the market is in need of housing?

Are you having more success sourcing off-market properties, or do you focus on distressed opportunities through agents or wholesalers?

I’m sure he feels like he earned that money because of how much time he spent going to different sources supposedly.

Because if you make good money and always have a source of funds for emergencies then you can use the money immediately if you have enough for a down payment on another property or put it in a high yield savings account or treasuries for a low risk return with good liquidity.

I've flipped about a dozen properties here in Chicago, and quite honestly, it felt like something different went wrong on each one of them.My biggest piece of advice is to KEEP IT SIMPLE starting out. 

My point is cash flow is only one source of return on RE and in my opinion the least desired because it gets taxed annually.  

It would be smart to do a full lease audit, estoppels issued, and tenant interviews.And if you are buying cash, there is nothing mandatory, since it is your money at risk. but again, physical condition inspections, understanding of tenants (they are a great source of information about issues with the property that the landlord may not know or may not disclose), surveys to understand accurate property lines, etc.

@Spencer DixonRecommend exploring as many sources as possible to get referrals AND cross-reference them to get as much accurate information as possible.Check out NARPM.com, BP’s Property Manager Finder (BiggerPockets: The Real Estate Investing Social Network), etc.Also, encourage you to learn from the mistakes of others - by reading posts here on BiggerPockets about owners not having their expectations met by their current Property Management Company.