The losses would have spiraled out of control for me had I not been able to sell my second house immediately.I don't look back on my experience with any regrets since I know the risks we take playing this game. 

Single family homes are exempt from rent control when privately owned.  

Neither VRBO nor Airbnb are vetting guests, either.The best you can do is have some internal controls, such as minimum number of nights.

Even large and small businesses with intangible residual services like TV, internet, security, pest control or the local contractor with remodels in process could fall behind on payments revenue contract. 

@Dominic CampeloWith your contracting expertise and business growth, you’re in a fantastic position to enter real estate investing.

Seller financing can be a fantastic way to get into a 4+ unit property, especially in a competitive market like Chicago.Have you started reaching out to owners directly or networking with agents who specialize in multifamily properties?

How much “control” are you willing to give up? 

They also are thinking of getting a different PM to manage it after they can gain back control but would like advice on doing so.

If there was no appreciation, there is no need to do a 1031 exchange.I have never been a fan of condo's as you lose some control over the investment - You have no control over the monthly maintenance fees, you may not have control over who is on the board, you have no control over special assessments.I wish the investments turn out well for you!

Based on what you wrote, it sounds like your project partner lost control and got pushed over by the contractors.