With the current environment I know it's going to be hard but I am just curious to see if anybody knows of any grants from the city of Los Angeles or the state of California (I know that's a long shot.)

You will have much higher bills with vacancies, roof, legal, etc.I think starting with an existing building would be easier than new construction, but a lot of projects in Texas are making great money just due to the environment.

If you are in a lower rent environment you may need to budget extra though.

By the way, I don't know your Chicago market/legal environment but one trip over to see 10+ houses and review of their $5-6k property taxes was enough to say 'no thanks' from an investment standpoint. 

Common strategies include assessing the job market (unemployment rate, median income), population (size and growth rate), rents (absolute and % of median income), and housing market (HPI change, housing prices, rent/income ratios, tax environment).Are there any websites that you have found useful? 

If you price a bit higher, you will get applicants who are more interested in the neighborhood, the house, the environment.  

There are many government agencies that are not going back to an office environment.

I would not do an 18 month lease in the covid environment with a tenant I don't know.   

So in this environment, do we sit on cash and wait or buy high?

With the inflationary environment were in, it's likely only going to become more costly.