Since I am strictly W-2, would it be smart to consider getting my LLC in order to protect my future investment properties, and while also reaping the tax benefits of having an LLC?""

Quote from @Jerry Zigounakis: This just in from proper insurance"Thank you for your interest in Proper Insurance® Due to strict brush/forest fire scrutiny, our program underwriters have declined your property coverage.

What are regulations like ?

I recommend you go to the source and educate yourself on all the landlord-tenant laws, particularly in an increasingly regulated state like Colorado.Here's a good starting point: https://doh.colorado.gov/landlord-rights-and-responsibilitie...

I am very familiar with the strict zoning laws for Hawaii short term rentals but most Waikiki apartments are either too expensive or leasehold only properties. 

Concern: NYC’s strict landlord laws, high purchase price would tie up capital & be in less desirable area, would likely not cash flow (not good when I leave)2️⃣ House Hack in LA – Move back, get a small multi-unit, and offset my mortgage with rental income.

Quote from @Joy Daniels: As a short-term property manager I've seen how this industry changes so often—new guest trends, tech tools, and regulations seem to pop up all the time.

You need a commercial investment-focused broker with no seasoning requirements or not as strict as standard traditional guidelines.

i set strict qualifications for my rental 3x income credit score of 700. 

If you're strictly buying turnkey properties and financing with DSCR loans, keep in mind that you'll typically need to put down 20% or more, and because of the higher LTV, you’ll often get the highest interest rate available for your credit bracket.