So if you are going to be a host that outperforms your competitors and want to get fabulous reviews, there isn’t complete down time if you are self managing at the highest level.

If you are looking to work with a STR focused realtor that probably has the most STR sales in the area, is an STR investor himself, has a STR property management company and assists with staging if needed, and can give you a true pulse on the market, I recommend reaching out to @Josh Green.

Random things like this.I can only imagine if they did allow you to add all the bedrooms, they would make you also add fire sprinkler system and a commercial fire alarm system like residential assisted living. 

Don't use overly rozy projections based on self-management and renting it out forever.2) Higher risk - how do you know which tenant caused the damages or brought in the bed bugs?

I currently house hack in Chicago, however, going from that to STRs where I cannot self manage is a different ball game and just wanting to pick peoples brains who are doing what I'm interested in doing.  

Offer to be his/her assistant for free, do all the stuff he/she hates doing, and learn the business from them.

My wife and I only have <5 properties we are self managing.

Make sure you've got cash reserves for closing costs (around 2-5% of the purchase price, repairs and maintenance (aim for 1-2% of property value annually), vacancy periods (budget for 3-5 months of expenses), property management (if you're not self-managing), emergency funds for unexpected repairs.When choosing markets, look for those with stable job markets, growing population, and strong rental demand.

If you build a good relationship with a local realtor, they can assist.

In terms of the second scenario, the upside I see is the option to get a different kind of loan (say, FHA with a lower down payment and other assistance programs for K-12 educators like me) since I'd be getting a new primary residence instead of a second home.