You aren't doing much mechanical work on a house in Chicago in that price point with permits, etc. 

There's been a couple that I've been tempted to try but I just don't know enough about the mechanics of them that I've been willing to jump in both feet, and dabbling to me seems a good way to lose your money.

01) Property Info         01) Insurance (at top as most important)         02) Property taxes         03) Deed & Title         04) LLC Docs (if any)         05) Purchase-Sale Docs      02) Utilities      03) Maintenance      04) Leases         Lease Name Folder            Application Docs      05) Advertising      06) Rental Licensing (required in most of metro Detroit)      07) Inspections      08) Appliances & Mechanicals

These large buyers/owners would discover that no matter how much they controlled their processes, it was extremely common to have multiple houses in the same neighborhood (or even on the same street) with dramatically different floor plans, mechanicals, and finishes.

But as far as the mechanics go - a 1031 might be available.

So far, I'm attracted to wholesaling as it seems to be both a simple entry point and a way I can stay debt free.I'm a highly mechanically minded and detailed kind of guy, so understanding property condition and data processing is of no concern for me. 

The mechanics of real estate investing is easy.

I looked heavily into building an HVAC program to act as an employment pipeline when I was a mechanical contractor.

Just finishing up my first flip and I wish I had known more on the age of the roof, mechanicals/utilities with pictures of all of them.

The "effective" way to start (not necessarily the best "legal" approach) is to have the LLC file a mechanics lien against the property before it gets sold or is further levered.