How do I help this person and not sit with property for an extended period of time before starting construction?  

As you mentioned, residential properties depreciate over 27.5 years, while non-residential properties depreciate over 39 years.If your short-term rental only averages 30 days or less as an average rent period, it would classify as transient.

Additionally, it can help maximize renovations and improvements.A Cost Segregation study is an IRS approved federal income tax tool that increases near term cash flow by utilizing shorter recovery periods for depreciation to accelerate return on investment.

It is important to be comfortable with "worst case scenarios" whenever you are investing - period. 

You need to look at your risk tolerance and what your numbers would look like if you got stuck with the credit card payments for an extended period of time beyond what you expect.

However, the greater metro area’s median home price remained unchanged at $450,000 over that same period.

Other than that, unless you want to do the landscaping periodically yourself or pay someone to, I'd keep it simple and functional. 

And maybe reconsider your tenant type if you need to spend a few days out of the year or periodically dehumidifying the place?

Tenant appears in court and requests for a trial.

@Jon Mekeel - I'll give you two-in-one answer: get on the list of all wholesalers you can find and watch their emails - periodically, one will make the mistake of sending one with their whole list of recipients in the TO field.