Years went by and we never agreed upon a price, didn't speak often and I never had any dealings with the property.

I have not walked the property, only drove by the location so I can not speak to some of those vital questions that you inquired, but the location is really good, and the structure from the street seems solid, with a newer looking roof on one of the units. 

Feel free to reach out if you want to speak to someone local.

Finally, attending local real estate meetups and speaking with other investors is another way to learn your market.Happy investing!

First, speak to your agent.

I want to make sure that I don't fall victim to analysis paralysis and so I have decided to reach out, speak up and get active on the forums - to learn and also, hopefully in time, contribute in a meaningful way. 

Generally speaking though hard money isn't something I would recommend for a live in flip.

I can't speak to the Naples area but I know that Destin is one of the best short term markets in the country per a number of market reports I've read. 

Little pieces will break off and cut your arms and legs and it will get bloody quick, speaking from experience.

Ask as many questions pre auction as possible at county office and speak to local realtors about land sales.