Based on my calculations it seems a bit overpriced.

Too many facts and each company will be different based on size of project, single family or multi family, single property or multiple properties, etc.

My wife wants to pay down debt first then consider buying a second home, especially with a baby on the way.

If it is simply the house and the tenant pays all the utilities, I personally would not charge more because you are renting them the house-not based on how many people are living there. 

Ft Myers Beach regulates the minimum stay to daily, weekly, and monthly based in the street the property is on.

You could have a case based on misrepresentation if the seller, acting as an agent, falsely claimed the roof leak was fixed.

Where are based out of?

Ceiling white matte, walls Navajo White eggshell, trim base white semi gloss. 

Best guess of his reason for selling is that he bought it low and during covid, stuffed every unit and room with a tenant on a month to month basis and now wants to sell at the max price based on the comps of the area.

Regardless, you will likely be adjusting the expense base to reflect the tax reassessment (which you can obtain from the local county), insurance (from your insurance broker quote), property management fee, and usual repair/maintenance expenses/admin/advertising/contract services/utilities.