Anti-landlord laws and bad tenants have taught us a lot, particularly that there are much better areas for cashflow with a lot less headache!

And with the city seemingly so anti-Airbnb, you still have to worry about the regulatory certainty.

There is also rent control, and anti-landlord politics that I would have to deal with if I decide to rent it out or go multifamily.

You can either pay upfront with money for someone who really knows (who is actually educated themselves) to show you or teach you, or you can pay with time trying to sift through all the available information trying to determine which information is correct and more accurate, or you can pay on the backend as you pay to fix your mistakes.There are so many people here on BiggerPockets that are anti paying for education.

The point of focusing on vacation rental markets is in most cases, you don’t have to worry about anti STR regulation.

Once the oxidation started, it can be difficult to stop. 

I just don't get why certain areas of the country are so Anti STR. 

(If you are anti-mac get a NICE PC laptop.

UPDATE: I posted this 5 months ago and a left wing anti landlord contacted my employer and told them that I was wanting to quit within a couple years.

Yes, you would still have to pay income tax on it, but you would likely have deductions from the home purchase to offset some or all of it.Here's a link to the IRS's Exceptions to Early DistributionsClimbing atop my anti-traditional 401k soapbox: cash out and don't look back.