I would go with your gut on which home you would rather live in.

Large wrap-around covered porch and a small flat yard to enjoy the amazing views.

Feel fre to pm me any time I enjoy figuring these things out. 

I originally lived in the casita while I rented the front home out.

I prefer/enjoy STR Like the Best with Michael Chang.

Similarly, you can offset credits from the activity against the tax on up to $25,000 of nonpassive income after taking into account any losses allowed under this exception.If you’re married, filing a separate return, and lived apart from your spouse for the entire tax year, your special allowance can’t be more than $12,500.

What I've found so far is the property has to be self-managed for the first year and you either need to live in it 14 days or 10% of total days it was available to rent, whichever is greater. 

Obviously you’d never sell until you’ve lived there 2 years, that’s a 5 figure mistake. 

Many local people own vacation rentals and make their living renting to tourists, as I do.

I live in Oregon.To summarize:1.