If you're a carpenter by trade, you may be short on money but have a lot of skills useful for flipping or renovating fixer-uppers.

The Chicago Neighborhood Initiative has rehabbed a decent amount of homes on Champlain and Langley, and 30 more distressed assets will be coming alive shortly, so there is progress - https://www.chicago.gov/city/en/depts/doh/provdrs/housing_resources/news/2020/july/city-grant-approved-to-restore-30-historic-pulman-rowhouses.htmlYou are right, inventory is extremely rare down there as it's tight-knit, not a lot of trading, and when it does, owners tend to trade with each other.

The trade off here is that investing in RE is more work than stocks. 

He is more knowledgeable and has connections with trades. 

The new CPE (core inflation) and CPI inflation numbers just released on thursday so its your lucky day and rates have dropped to the lower 6's (prior was around 7 or little over - range).Once monday mortgage bond market opens at 630PST or 830 CST yourtime you'll have different pricing so definitely check in on monday and to accurately compare you'd need to get everyone's quote at the same time and same day because the mortgage bond market trades in real time and could reprice multiple times perday.In the end most lenders should be so close that you'll want to work with the best you can find.Hope that addresses the real life situation of conventional mortgage pricing (bank and portfolio mortgage prices change a lot less frequently and is another topic for another time).Best Regards,@Matthew Kwan@Carlos Valencia

I trade rent for 12 hours of handyman services per week-- but I wouldn't do that until you find a really trustworthy handy person.

Challenges - Since this was our first property, we did not have a contractor, plumber, electrician in place and finding these trades was challenging as these trades are extremely busy at this time.

So when something so obvious to crash, was only recognized and accurately forecasted by a barber-shop quartet, how safe and certain are you to wait for the next drop, and how accurately it will be forecasted and projected?

I paused that because I don't enjoy the market research and selling side of it, but when I dig deep, I realize rentals are not going to be any more enjoyable in those aspects (trade selling with renting/managing), and would be even more hassle in general.  

We are both nurses with good income but don’t want to trade dollars for hours.