If I was to trade a $300k house for a $310k house that will cost me $10k and $347/month what amount should I ask for to make up for these losses?

This implies if you sold and bought the exact same house your current property tax would increase substantially.  

I own a house in North Port, Florida (right on the border of Port Charlotte).

The unit shares the same heating and cooling as my own house.

Have you sent your material list to a supply house to be quoted, have you arrived at a quote with your subs?

., desks and Wi-Fi for professionals, cribs and baby gates for families).Evaluate Your Own SpaceYour property’s layout, amenities, and location may naturally cater to a specific audience.A cozy 1-bedroom apartment downtown might be ideal for professionals or couples.A 3-bedroom house with a yard might appeal more to families.Proximity to nightlife might cater to party groups.Experiment and AdjustIf you're unsure, start broad and monitor who books your property.

Away from the coast, no hurricanes, fires, floods - we don't even have snowstorms anymore.People can deny climate change all they want or blame it on sun cycles, and frankly, it does not even matter, the reality is that insurance cost will force the issue.You can try to rebuild and you can put houses on stilts in flood areas, or fortify them against high winds and fires, but that makes it expensive.

I've been outbid on a number of houses by banks. 

I am looking forward to buy  my first  condo or a town house in fort Myers/ Bonita spring area and would like to rent it out when I am not in the states.

@Ryan Daulton,You don't have to buy a house in SDIRA without a loan; you can easily get a loan, but it must be non-recourse.