Not sure how old you are, and $200K in a 401K may be a little or a lot based on age, there may be so many implications taking out money from your $401k, especially if you are still working for this company.feel free to reach out for tax advice

I would only underwrite based on actual rents not proforma.

There are way better people to talk to that are based out of here and know the market like the back of their hand. 

Also , I would love to connect with any agents who specialize in STR market in Boston Mass area. airdna is pretty accurate . lenders use it to assess rental comps for short terms rentals when financing a short term rental  I use it for DSCR loans as well; it is accurate yet conservative because it gives you the median 50 percentile for the area based on comps.

We are seeing big increases in HI because of the natural disasters in FL, CA, etc.

This is a passive way of earning with real estate-based security, protection and insurance.

Real estate is not my of my knowledge base at all but I want to start working on building passive income now (I’m 44). 

Dwelling (Building coverage)The limit should be based on the Replacement Cost of the building (cost to rebuild withthe same kind and quality excluding the foundation)2.

Overall, these measures underscore the federal government’s effort to alleviate the financial strain on those affected by natural disasters.

This allows you to invest in the locations that offer the best ROI and make the most sense based on your goals where you can be a bit more passive in your investment property.