Just ensure that your increases comply with local rental laws and regulations. 

Yes this strategy works great especially if the numbers don't work locally.

To get a good rental income, be sure to check who you rent to very well, write a clear rental contract, take a security deposit, make a smooth way to get rent, keep the house in good shape, think about getting landlord insurance, keep talking to your renters, and follow local rules strictly.

I just let Airbnb do their thing and do my normal due diligence on Airbnb guests like asking why they're coming, making sure they have a valid ID and try to avoid locals unless they have a good reason like home shopping

I took the opportunity to venture outside of the hotel to look at the local real estate market.

Your answer would be it depends on a million things.Like the specific property, its condition, location to desirable areas, local STR regulations etc.We would need much more detail to be able to help.

Do a thorough market research and consult with local real estate professionals.Good luck!

My hope is to begin building my portfolio (probably fix/flips) this year while I continue to work with local investors on helping them build theirs.

Here some of my advice first Educate yourself Understand the local rental market trends, property values, and rental demand.

Talk to a local lender to know what you can afford.  2.Research how to do real estate transactions, get a good RE lawyer or find a good investment knowledgeable agent.