Let's start there and perhaps I can guide you in the right direction. 

Cash invested: $20,000 Duplex on Airbnb with one side “Girls Trip” theme & the other side is “Bachelor Pad” themed.

Do yourself a favor: buy "Every Landlord's Legal Guide" by NOLO.

I currently lean toward upstate NY and MI (Detroit metro) as I live in the west but have family in Canada not far from those locations and the idea of being able to visit family with trips that can double as business write-offs is appealing.

They would be the best bet in guiding you. 

Yeah, here is the passive activity Audit Techniques Guide which is interestingly not available on the IRS website any longer.

It's great to have you here.Here are some recommendations for you:Find and connect with other BP members that are in your area: http://www.biggerpockets.com/m...Set up keyword alerts to be notified of the topics that interest you: http://www.biggerpockets.com/a...Read Beginner’s Guide: http://www.biggerpockets.com/r...Check out BP Money Podcast: https://www.biggerpockets.com/..Wishing you the best

Setting clear goals will guide your investment strategy.

Also we created a free Memphis zip code guide that I can send you if you DM me. 

Of course, not as directly labor intensive as what you are embarking upon, good luck in your endeavor.Amazon.com: The Hands-Off Investor: An Insider’s Guide to Investing in Passive Real Estate Syndications: 9781947200272: Burke, Brian: Books