What's the best way to navigate this situation regarding the application process as well as the lease administration?

Better education and training might be one way to improve the situation  Damn, sorry to hear that.

I'll tell you how we do it here at CrestCore, and this is the case in many situations.

How would the situation differ with a home that’s never been a STR but would become one, or a home that’s for sale now that is a current STR.

It was at that point that we decided to pay a bit more and put more money into our deals for properties that only needed cosmetic upgrades or maybe a few weekends of work vs. rehab projects.Again everyone's situation is different and for those who have more time then money this strategy might not be best. 

But this was an awesome opportunity for me because this is my first living situation where I will be on my own (and getting used to paying a rent/mortgage) but this will put my overall mortgage on a 400k house at roughly $2000 a month for the first year!

The 2008 timeframe was different and in situations a lot harder than now, but this market will shape a lot of investors that found their new market, product to focus on, and/or to dive in deeper when times get tough.   

Whether you need a CPA with just three rentals depends on the complexity of your situation and your comfort level with DIY tax prep.If things are pretty straightforward, you might be fine with tax software for now.

The storage closet is storing a shower head, a toilet, and whatever else you threw in there.

Today I had a new situation and obviously can't advise on tax/legal matters, but hoping to get some insight from the community.Managing a property for a client who divorced her domestic partner last year.