Plus, you could also have your tenants reach out to the Cozy support team f they are having trouble. 

It seems to me to be incompetent to go through so much trouble causing me fees but not to go through the trouble of emailing me.

It's a win-win.The difficult part is proving you are worth the trouble.

The main plus it has for your tenant is that the lines of communication with the landlord are open and accessible.But here's trouble, and three months into the lease now, your new tenant  gets a lesson about how you handle trouble -- you send an impersonal, officious letter highlighting section 19B and 21A of the lease to demand payment. 

New to this and want to do a house hack but also concerned because I don't want to cause any trouble. 

If you believe your other tenant is simply a complainer out looking for trouble do not renew her lease when it is up or you will continue haivng tenant issues.

USLI or PersonalUmbrella.com are where most investors find umbrella options.They can do multiple states and group LLC's and personally titled properties on the same policy. thank you, usli reached out to me so hopefully they offer a good quote. i was on fence as i already have 1mm liability per property so wasnt sure if i needed more umbrella

Is it because $200 is a small amount and/or not worth the "trouble" to question it?

Will a a typical local bank give me trouble about a cash out if they see I took out a 20k personal loan even if I own the property free and clear .

Greed will get you in trouble!