Do the Airbnb discounting, price a little under market, make sure your cleaning fees are at or below average, looser cancellation policies will all help.

Quote from @Jake Thorpe: In this industry, there is a lot of incentive to bend the truth, some say dont say x to the lender.. and if something happens dont say y to the insurer. 

I’m a lifelong learner and exactly doing what you have all suggested- reading, researching, attending meetups, plan to attend conferences etc so I can continue to grow and be knowledgeable in this industry.

A paid off property at 5-6 cap rate should also appreciate at about 3.4% per year on average, so my real estate return at 8.4%-9.4% is reasonably close to what I'd expect in the stock market, and the income is tax advantaged.

Real estate investing is forgiving; the average person can still make money even with some big mistakes. 

The state has always had many hurricanes and while insurance here is higher than the national average, our housing price to amenities ratio is one of the highest around. 

., and well above the national average of 4.1%.

I work a lot, probably more than the average W2, but we also travel a lot, at least 6 trips every year.So that's what's driving me, numbers on a screen are nice, but they are not fulfilling on a personal level.

I fully renovated the upper unit with well-above-average finishes, and it's been averaging ~$2,850/month in gross rental income over the past 12 months as an STR on Airbnb. 

The rental market here seems to be cooling and it's hard to pencil deals even if I rent by the room to achieve higher than average rents.