Let's connect as I travel there about every quarter.

I work a lot, probably more than the average W2, but we also travel a lot, at least 6 trips every year.So that's what's driving me, numbers on a screen are nice, but they are not fulfilling on a personal level.

Many of also argued that forcing out many STR's will impact our tourism revenues, which we're very dependent on, as many travelers won't come here if they have to stay in a hotel.

See below for explanations, with headings taken from the attached document.Broken windows or exterior doors-The two narrow windows in the living room do not fit into the walls properly.

When do they start exterior work and how long to finish?

It could be worth transitioning to a midterm rental if there's demand for that type of housing in your area, like traveling professionals or remote workers.

Not sure her “design” fee or what was spent on travel. 

In rare instances we will let someone pay through Square or Stripe, with them paying the cc fee, but only in unusual cases, such as one time with a tenant who was traveling and didn't have a bank account to use with our online platform.

I’m self managing myself but the tax side of it is a little confusing to me but I’m recording everything involved as far as maintenance, traveling, expenses etc. just want to know what some people would do in my situation or what to I can benefit from come tax season  @Angelo LlamasI recommend that you find a real estate accountant to help you understand and prepare your taxes.Bigger Pockets is a great place to find a real estate tax accountant. 

If I may, let me offer some tactical advice and then some unsolicited general advice.Tactical advice: marketing to traveling oil industry workers probably isn't radically different than what you have been doing to get your rooms filled with students.