And rehab and treatment of back willbe more expensive than not having a job.

You are correct that the tax treatment of Airbnb business (emphasis on "business") is distinct from other forms of real estate investment - and that you should get clarity about that to incorporate into tax planning and investment ROI analysis.

Rul. 8429039, provided that a two-year holding period is sufficient to ensure treatment as a tax-free exchange (all other tests being met). 

Now 1031 exchanges may only be done on investment real estate.What still has to shake out is guidance on what the difference is between equipment and fixtures that remain personal property and so are excluded from the 1031 exchange, and equipment and fixtures that become part of the real estate itself and so eligible for 1031 treatment.

For example, repeals of the current annual property tax increase limits, or even limits on rental income or its income tax treatment in the state. 

Have a termite inspector evaluate it and he can give you an idea of the extent of the damage and can give recommendations on treatment.

Window treatments are depreciated over a small number of years, but only if you're doing a bunch of them.

Whatever you choose, though, you will generally get better treatment and terms, and develop a stronger relationship with a lender at a credit union than a bank, because of the cooperative ownership and not-for-profit structure of the former.

Since the sale of the property occurred towards the end of the year, in October, the 1031 Exchange was going to receive an Installement Sale treatment and in the event a Like Kind property was not purchased within 180 days the proceeds would have been taxed in 2018.

So far I have been looking at Bend, OR, Sunriver, OR, and Palm Sorings CA.For example: In Sunriver, OR I am finding that it might be difficult to pay off my mortgage and monthly expenses via renting which to me seems like it wouldn’t be a smart investment then.