I made the mistake of letting someone get in one of my first units that was a bit off the 3 times, they were great tenants very kind and enjoyed their stay and experience with me, but could not afford it when I increased the rent on them, which is something you will have to do because of rising insurance/tax costs.5.)

You need to have the income and tax liability to support the depreciation.

@Placeholder PlaceholderOne word of caution I would advise: If a community or local government is enacting restrictions and also regularly enforcing them, then its often a reflection of the local community sentiment which increases the chance of a neighborhood or nearby resident calling you in if they think you may be running an STR.

Taxes were $1363 a year.

@Roger D Jones and @Dominic Mazzarella hit it on the head: try seller financing first and see what his cash flow needs are and/or if you can reduce his CG taxes. 

The taxes and insurance sound like where we are in St Augustine and NY. 

a lot of people will poo poo this, but I also live in a market where cash flow is low, property taxes are high and properties are expensive (which is a relative term).

There will be no assessment for increase in taxes or insurance so remains at $1935.

I have a followup question - I will realize a lot of capital gain from this home in Idaho, so I think unless I purchase a new primary residence I will have to pay that capital gains tax. 

STR seems to have better tax benefits (in the right market) but is it worth it at a distance ???