Quote from @James McGovern: Landlords typically care to understand when a prospective tenant has been evicted indicating they are problematic, however landlords lose visibility if a tenant has been asked to vacate outside of eviction.

I'm not concerned so much with issue #2 that he raises since you're calling it a vacation rental. 

Each cancellation was for a personal reason like a new job with no vacation days etc.

For a new primary residence or any kind of investment/vacation property on a Conventional loan, you'll need good personal income to qualify.

Quote from @Michael Baum: Hey @Sushil Gupta, important statementCity No Longer Accepting Applications for Non-Hosted STRs:To apply for a Hosted STR, the property owner must live and sleep on the property, and the property must be the owner’s principal residence (where the owner resides for more than one-half of the year)So unless you plan to live in the place you are short term renting, Santa Rosa is a no go.https://www.srcity.org/3625/Short-Term-Vacation-Rentals one might try Guerneville or Monte Rio  area that is geared towards tourists..

Quote from @Bruce Woodruff: Careful - a guy building a vacation home was mauled and killed a couple years ago in Prescott...just having his morning coffee....and all of a sudden bye bye...https://www.nbcnews.com/news/us-news/deadly-arizona-black-be... yikes 

I also operate in a New England market (downeast Maine) that has the old, legacy vacation rental feel to it.

I provided 60 days written notice of them needing to vacate even though our lease only requires 30 days written notice.  

My wife and I have built up some significant savings and are highly interested and excited to purchase our first STR in the near future.We enjoy the pan-handle of Florida as well as the Southwest coast (Cape Coral, Ft Myers, Naples).  

• Rental demand insights (both long-term and vacation rental markets)?