I do a lot of business on the nearby barrier islands of Anna Maria and Longboat Key.

Since April of this year, they have consistently been paying rent late in partial payments.

If anyone recommend any investor-friendly Title Company who can do double closing in Long Island, NY please drop some comments thank you!

Consistent rent growth can signal strong demand.Job Market & Population Growth: Rental demand often follows job and population growth.

When I evaluate the options, house hacking consistently offers the highest risk-adjusted return, 10 times out of 10.That said, it seems like house hacking might not align with the lifestyle you envision: “I can’t afford a place with enough bedrooms in a single unit in the areas I want to live.”

Also I am thinking I can expand to Rhode Island, New Hampshire and Connecticut which are close to MA.

Similar to you, I wanted to find somewhere less expensive, still close to the Bay Area (drivable), but without the high property taxes, more favorable tenant/landlord laws, no state income tax, and consistent job/population growth. 

@Dayana Castellon, managing cleaners to consistently set up and clean the Airbnb worth a 5-start rating.

This team consists of an Investor Focused Agent, Lender, Contractor, and PM.Read this article on the "core 4".

Sentimental value can be a significant barrier to selling, so creating a level of trust and understanding is crucial.One strategy is to consistently follow up over time without being pushy.