We both live in MI and my current plan is to invest in single- and multi-family in solid, path-of-progress neighborhoods in metro Detroit, and also get some larger SFH's in the more expensive market where we live and do rent-by-the-room/co-living.

My current flip was bought from a wholesaler in a partnership with a builder friend of ours who has his own salaried framers, roofers, plumbers and electricians.  

Can you either rent out your current property if there’s been little/no appreciation, or sell it tax free?

I currently have a pre-tax retirement account with employer match and a Roth IRA invested in the stock market.

The whole ecosystem (and trades) is valued at hundreds of billions, but most participants bought in at well below 1/10000th of current prices. 

Given that the property was worth $390K in its current condition, I saw an opportunity to make the numbers work while keeping my upfront costs low.Instead of increasing my cash offer, I negotiated a $25K down payment with the seller carrying the balance for two years through owner financing.

This is the silver lining to our current market.

The current owner lives there and had someone paying to a trailer in the back yard all the way in the back. 

Aim for a path that benefits the current tenants if it's worth it.

Is this a home that you are currently living in?