Again, I am extremely new to this concept so my questions may sound uneducated and simple.

One that is typically in a good neighborhood that is extremely run down, outdated, damaged, etc.

When you finally stop, they'll hate you for it much more than if you were cold from day one. 

There was a ton of mold issues as well and since the house was well known to the town inspectors they extremely vigilant on the work we were doing causing some delays.

Fire and wind insurance in FL at $70 seems extremely light. $120-150 seems more realistic.How do the numbers look after that?

@Joey Walker Specific parts of Spokane are extremely hot right now for MF and still seem cheap compared to Western WA

Be EXTREMELY careful when renting to friends. 

This information is extremely helpful. 

However, it would be extremely rare for this to apply to short-term rentals of your home or second home.Exception to the Significant Services Rule – If the personal services provided are similar to those that generally are provided in connection with long-term rentals of high-grade commercial or residential real property (such as the cleaning of public areas and trash collection), and if the rental also includes maid and linen services at a cost of less than 10% of the rental fee, then the personal services are neither significant nor extraordinary for the purposes of the 30-day rule.A loss from this type of activity, even when reported on your Schedule C as a trade or business, is still treated as a passive activity loss and can only be deducted against passive income.

@Alexander M Dant Real estate investors are everywhere regardless if the cost of living is extreme.