Our plan is to move forward initially with buying single family homes in the Chicagoland area, and then use the BRRRR method to raise the equity in them so that we can grow larger and larger by buying properties with the increased equity seen after each renovation.

One noise complaint from a neighbor and you can lose the income.I feel the same about air bnb, make sure you are ok with the rental by itself as a long term rental, in case any income you get from an adu or air bnb goes away with a city ordinance.Sounds like a marginal deal without, and a nice kicker for upside if you include it.We would probably do the deal if it was currently allowed by the city, especially if it was in a growing area metro area

Looking at those factors, I felt more comfortable leaving my cash in the stock market- growing it slowly until i found a deal that would cash flow better.I finally decided to look out of state.

@Mark Ainley,NARPM is a great organization for property managers who want to learn, grow, and build relationships! 

For investments that are relatively static and singular in nature - shares of a private placement for example - the services of a self-directed IRA custodian can be sufficient. 

Or else is it just the crazy SF Bay Area market with overvalued properties that naturally sell higher than the rental market can bare?

Syndicators like me are always looking for new partners in various metropolitan areas to grow our portfolio together.Cheers, Ken ;-)

Wanted to grow my network in my hometown, as well as better understand what challenges you all face and how I could help.

Does the site have access to electrical power, natural gas, town water or sewer?

I really cannot speak to other investors' reasons for contracting homes and backing out, but I would think it has more to do with the condition of the home rather than the laws.If you're looking to buy and hold, you need to know that there are some areas of the south side that won't expect to appreciate but WILL cash flow a good bit, and there are other areas that are currently growing tremendously but won't necessarily cash flow as much.Are you looking to buy in this area?