Adding a 2nd story is tough on aesthetics very rarely do they turn out great. 

I rented a house myself during my Senior year in college and had two roommates (both of which were my friends).I agree with @Annchen Knodt - renting by the room would be tough.  

@Antonio Ramos any evictions in Ca will be tough if they happen at all.

Supposedly good rental market for blue collar Chicago workers.

The tough part about a database is getting it up and running, and the data entry. 

@Lee Jedlicka, wow that is tough!

Taking the first steps toward getting listings seems tough so far but I’m staying optimistic and reaching out to people where I can ie.

I have also developed good relationships with local contractors and know quality workers. 

I'm sure this thing is tough on a lot of people who were not prepared for it financially, or supply wise (W2 and Owner Operators both).The mandatory stay at home orders, food shortages, TP shortages, job loses, the uncertainty of your financial situation, having no job, or having to let some of your people go, etc...But it will end, and it may make it more endurable to focus on a possible end date. 

MA, from my limited experience, is a tough rental market in general with the high cost of properties.