What makes a property with no mortgage more attractive than one with $1000 mortgage outstanding?

Also if they are really old wood frame yea they are a pain to deal with not to mention poorly designed most can be unlocked from the outside with a thin putty scraper so i would never live in a house like that because i like to open and close my windows withough having to remember to put a pipe or wood block back as a secondary window lock

I have an Electrical Engineering degree but haven't designed anything in over 9 years having moved into more of a project management role.

Not to burst your bubble however it doesn't work that way unless you can attract clients because you have become an agent rather than being one.

Should I buy something in a less attractive neighborhood?

I have deals in place waiting to be unloaded to any buyer who has a need for these beautiful properties (I will be designing each property myself, yes and you're welcome)!

I have even seen inside floors stained, and it was extremely attractive. 

Miami is been talking about casinos for years and it does not seem to be happening in the next few years, Cuba will attract a lot of visitors looking for the Caribbean Vegas, especially now that new charters have been issued for some Cruise lines and ferry companies.

The cost of other (non-new construction) houses in the neighborhood have no relationship to the cost you'll incur to build a new house.Your costs will be based on a lot of factors:- Location- Level/type of finishes- Style of house- Size of house- Whether you GC it yourself or hire a builder- The types of contractors you use- Your negotiating ability- How strategic you are with your designs to keep costs downI've built houses for $60/sf, and I've built similar houses in other locations with different contractors for $90/sf. 

We've staged before and it's about 2k for design / delivery / haul away and 1k a month for rental.