If they are uncomfortable with that, they can call the police.

You will learn so much and become more comfortable living in the uncomfortable.

So while I  didn't think you routinely spoke to them about her situation I got the impression you were planned to approach them on the termination at some point based on the above statement.  

One piece of advice I came across early on was to always raise the rent every year, even if it was a a token amount, because it gets the tenant used to annual increases and avoids the uncomfortable situation you are in (because you are a compassionate person).

It was a routine my former business mentor suggested I do, and I've been doing it for awhile now.

So will you need an office, hundreds of staff, and have to go back to wearing uncomfortable suits again?

I've always been really careful and feel like I should get a break given how long I've been living here and how few issues I've had due to being so gentle (10 years, never complaining about anything even when it's routinely 58 degrees in the winter and as high as 92 in the summer).

Be comfortable being uncomfortable.

I gather that most of the people who posts here has had been experienced in short term rentals so i decided to seek your wisdom on the current dilemma i have. just for background info: i have an STR in big bear ca that i have been operating for a year now. i had utilized evolve to handle all marketing and reservations and it has been ok so far. i have an upcoming guest that is supposed to check in on december 26 with a reservation for 4 nights. those dates are the highest priced days in big bear. i has been my routine to email my guests check in instructions 3-4 days prior to check in. when i did that to her, she responded back stating that she was trying to cancel for a couple of weeks because of sickness in her family and was trying to cancel. i checked with evolve if that was true, they said she never reached out to them and that she opted to not get travel insurance so we are not liable to refund her anything but it is up to me if i want to give her back a portion of what she paid. now this is not the first time this happened to me, another guest tried to cancel last minute to me a couple of months ago requesting that they get refunded even without travel insurance which i did (a portion) since she did it a week prior  and the dates were not so pricey as this one. and she had a sick relative too!!

After just meeting with her, she explained that she’s fully aware of everything in the contract and laws in Texas, and she’s done her own research on what’s happening with the other half of the condo and that she discovered how much the other unit now “owns,” and this makes her too uncomfortable to stay.