You need to know how to analyze property and then systematically evaluate property on a daily or weekly basis to stay on top of the market. 

Smart move. documentation is your best friend :)  Stay safe out there.

They'll moisture meter everything affected to see if it needs to be removed or can stay.

I’m curious - are you leaning toward staying local in Connecticut, or are you open to exploring oppurtunities in out-of-state markets like Phoenix?

If she's staying another 2 weeks, charge her what the rent would have been for Jan. 

Otherwise with the dwindling tech sector in SF, and the remote work (2-3 days a week) that is most likely here to stay, it just doesn't seem like a strong mid term market to me.

Generally in Illinois, the Tenant does not have the right to cure the lease violation and stay in the property.

Quote from @David Martoyan: For those focused on the BRRRR strategy, I’d love to hear about how you’re adapting to current market conditions.

He was happy to allow me to rent out nightly because it actually helps keep his property in better shape than a long term renter (having a cleaner in there every turnover, short stay guests always let you know when something isn't working, etc) but didn't want to hassle with worrying about a percentage of income/management, etc.

As long as you stay invested and let your hard earned capital continue to grow, you can pick your spots when a real estate opportunity offers outsized returns comparatively to other investments.