Hi @Evan Coopersmith - Even though you aren't currently interested investing in Chicago I'd still suggest looking into some of the local meetups here! 

If you aren't a contractor or aren't getting rock-bottom pricing, what is the point?

It's a matter of finding the one where the weaknesses are in areas that aren't relevant to your needs and/or don't aggravate your personal pet peeves. 

Tax-Free Exchanges: While 1031 exchanges aren't available to SDIRAs, the tax deferral within the account means you can sell property and reinvest proceeds into new opportunities without immediate tax consequences.

They aren't the actual bank so need to upcharge these fees and hoping in volume they can make enough to continue operating. 

There aren't many lake front properties in that area for sale, but there are a number that are in the 800k range.

Hang out with others that are doing what you want to do and invest your $25-$50,000 in real estate vs education. 

They could include things like waivers for documents and appraisals, relaxation of underwriting standards and money to fund repairs.However, there are benefits for people who just live in the areas, but aren't directly impacted.

It looks like most of them have been listed for 2-3 months, so you aren't unique.Another consideration is your distance from the city. 

If you are saying you want to be making 350k a year from real estate before you leave your job, you have a LONG way to go and aren't thinking of it the right way right now.