This is our boilerplate language:Insurance: Tenant should obtain a renters’ policy of insurance on their personal property.

I want to exit as I don't get any personal use from the STR being 20 mins from home and would rather apply the capital to another opportunity in multifamily (LTR) or another STR in Hawaii where my brother is a broker and now manages STRs.

But I don't know your personal situation and all the financial details. 

Also, long term, I expect Sac will enact tougher restrictions on STR, given the intense housing crunch we're experience, so I personally don't expect that to a be a good long term strategy.

If you have a chunk of money to get going I'd personally buy the biggest thing you can if you don't I think house hacking into a 4 plex is great. 

I have been to a few of them personally its really something and the folks that own them are under the radar and make MILLIONS.

My question is if she doesn't pay in 5 days, could I file a forcible entry detainer at the court ( We are in Macoupin County Illinois)?

Choose a goal so ambitious it forces you to grow into the person who can achieve it.

This is advantageous bc later you have a third party loan (not your personal money) so seasoning period is 90 days to DSCR out. 

I haven't personally dealt with any crazy insurance premiums such as the ones people have been advertising in like Tampa, FL.