I recommend this and plan to run my "final" lease by a local attorney to ensure it's adequate.

Is it listing your property, generating leads, deciding on an adequate listing price, tenant screening, uncertainty / fear of selecting a bad tenant, rent collection, etc.? 

You can cash-out refi deals with adequate equity for a tax-free payday or to reinvest earnings.

Or back to your original question if you don't get the comp data that you need to adequately value the property then you could use a gross rent multiple on potential and actual rents for your valuation.

Perhaps you need to adjust your rates, or develop a more complex and targeted rate strategy that adequately captures peaks and valleys in demand. 

So based on your hypothetical, person B should be more successful, granted they have adequate negotiation skills. $1000 a month to start is fine.

Make sure the decking is adequate for hurricane requirements. 

I did a perfectly adequate job doing it myself and I'm not that skilled.Like the others said, I'd look for an all-inclusive quote.

Until you have a toolbox of knowledge adequate to help you understand all of the basics of real estate, lending, investing, etc., you're not ready to invest.

There are smaller towns in my area that are decent, some booming, your population seems more than adequate.