Homeaway is probably 80% of our bookings anyway and tend to produce better guests for our high end properties.

Many Many times as the leader of the local REIA in Kansas City, I would get calls from out of state investors who snapped up a turn key rental property for so cheap that rented for so high and produced $500 cash flow a month.  

I have a feeling if she had something she was able to get excited about (business, hobby whatever not real estate related, not necessarily income producing) she might be more understanding about what this means to you.

Here is the high income producing property in Ashview Heights that is off-market.

You wouldn't want surprised capex, surprised vacancies, unexpected expenses, ... etc.You should try and see if you can add additional income producing things (laundry, short term rentals, pets fees, RUBS? 

So I have a good problem...I am running 2 short-term rentals and they are producing a large amount of excess cash which is currently sitting in a business savings account doing nothing.I have mortgages on both properties. 

You might want to poke around some and see if there is a company local that could actually produce better.

Emotions always cloud decisions and will very rarely produce results better than non emotion based decision. 

In that instance if it is financeable most of the cash flow would be going to service the debt for the lender producing very little cash flow to pay out on the property.If you pay all cash at a 5 cap basically it's 5%.

You can't micromanage these people.It's not a profit producing activity.You will go mad.Ask yourself this.How does the tenant being messy hurt your ROI?