Thus, I am looking into other options.I have come across a class C office building in a nearby city center, with parking.

I looked at it on Zillow and boy is it ugly and out of date inside.The home is only twelve years old but looks 25 years out of date.The kitchen and bathrooms are cheap and ugly,it needs better paint choices,laminate flooring and nice tile for the kitchen and bathrooms,new appliances,tiled shower instead of plastic,and new landscaping.Combine that with a bad foundation and too many nearby homes for sale in better shape and it's easy to see why this turkey is rotting.The bank is calling the shots so I would make out a laundry list of repairs and upgrades it needs and present it to the bank with an offer of maybe 110k and challenge them to argue otherwise.

I had been looking in one midwest market because of family nearby, and started to build my team.

It's a good idea to have a good renovation estimate when you look at properties.I also wouldn't dismiss other counties nearby like Ann Arundel or even Baltimore.

Location & Regulation: Research popular tourist spots, nearby attractions, and local STR regulations.2.

@Ryan Thomson is a house hacking expert nearby.

As @Arn Cenedella suggested, the initial courses are in depth and can be daunting for someone who hasn't studied a college level math or economics course in a while, but in person instruction is helpful if you can get to a class somewhere nearby you.

My ideal house is a 1200-1300 square foot brick 3/2/2 in a decent area.(2) Sub $130K ARV (much higher and rents start to taper off relative to value)(3) Newer houses are superior to old ones (and will justify a higher price) as long as there is not a lot building going on nearby that will suppress home prices(4) The result when I'm done fixing the home is that it has to be fully renovated and updated (no deferred maintenance or cap ex for the next five years)(5) I assume 1 month vacancy per month.  

I have known quite a few who have lived for years on primitive lots and pulled their trailer to a nearby station for emptying/filling.  

Best of luck and happy to answer any questions regarding North Naples or any other nearby area for that matter.