I’ve received multiple quotes from insurance companies (mainly I would obtain the quotes myself).

It’s a lot to keep track of, especially when researching multiple markets.Would greatly appreciate any advice/insights from experienced investors who've navigated these challenges :- How do you approach understanding and evaluating short-term rental regulations when considering a new market?

The sooner you use a system like this, the easier it will be to keep track of it all when you have multiple properties. 

I’ve worked for some group home providers where they employ a maintenance worker who handles some of these issues (usually if the have multiple homes in a specific geographic location) and I’ve worked for homes where the handiest employee fixes things and that option doesn’t always have the best outcomes.

The insights shared by the Realtors, @Zeke Liston, @Jimmy Lieu, @Nathan Gesner, @Samuel Diouf, @Sam McCormack, @Min Zhang provide a solid foundation for anyone starting out in this industry.From a property management perspective, it's great to see you're considering the long-term rental strategy.

I am also considering multiple rentals and it appears that I have found a pretty good property manager based on feedback I have. 

You can create multiple subsections. 

There are multiple billion dollar companies dumping money into the city, such as Intel, Google, and Amazon.I'd be happy to share some areas where you'll see the most cash-flow.

Multiple asks muddy the waters and make people feel as if you are nickel and diming them which you are.   

COMBINED FROM BOTH DUPLEX SO ITS ALL ABOUT PERSPECTIVE YES THIS YEAR WAS HARD AND HEART BREAKING BUT ITS ALL ABOUT THE RESPONSE AFTER GETTING KNOCKED DOWN !