Would you be better off selling and purchasing a less expensive property that would require less carry should it become vacant for some period of time?

The other thing to think about is the length of time you've owned the property.

However, they spend a ridiculous amount of time for 1-2 deals a year.

Thank you for your time and patience!

If you are setting aside funds for capex, taxes, insurance, or other expenses that don't occur monthly, transfer those funds to Savings each month and hold them there until it's time to spend them.

We work with people in your shoes all the time. 

Many of the OTAs and lead gen sites, like Furnished Finder, are pushing credit card payments. 99.9% of the time I get a message from FF saying 'your tenant would prefer to pay by credit card so activate Stripe now!' 

I had a mentor who stressed "you make your money when you buy"; the next place you get, be sure to haggle big time - and walk away if the price is not low enough.

I have a guy who has been here since July, but I renew his short term stay for two weeks at a time, every two weeks.

They preach that its not about the Real Estate yet there is alot of time spent on the real estate itself.