The risk analysis and mitigation is all over the map.We have done very well over the last 15 years.

We've had several situations where a potential client would tell us what we want to hear.

And if you make it a quid pro quo, don't you run the risk of violating the OTA's policy of paying to alter reviews? 

The agent says that conservatively I could bump it up to $1600-1800, with it being at $1400 would you say I should try to increase it to $1500 for next year and steadily increase it from there or make the bigger jump straight to $1600+ and risk losing the tenant?

You run the risk of offending tenants by asking them to jump through hoops again just to renew a lease. 4.

Correct - Track all your income and expenses.The bookkeeping will determine whether you are profitable or not.it will also be good to compare from year to year your income / expenses to see what expenses you can potentially try to limit.I.E.

Quote from @Reeti Peshawaria: Hi, I'm in the process of learning about short-term rental investments and analyzing potential markets, but I’ve hit a major roadblock: understanding local regulations.

Investors love to take advantage of this strategy to expand their RE portfolio and have better appreciation potential.

Nothing in the STR space is one size fits all, but the ideas can help others see the potential in their property. 

@Randall King If you find the property isn't performing well, a 1031 exchange would defer the tax and concentrate that equity into something that has a greater cash flow potential, like what @Corby Goade said.