These issues are hyper local, so you should talk to a good land use/planning consultant/civil/architect.

Gardner, MA$60,000 acquisition price$125,000 renovation budget$340,000 estimated after renovation valueThis is a property we are holding; we expect a monthly mortgage payment of $2,100 versus monthly rents of $3,000How we sourced it:cold calling non owner occupiersRenovation issues:Building department initially rejected our permit application because it was filled out incorrectlyBuilding department rejected our permit application a second time because it was filled out incorrectlyBuilding department scheduled a physical inspection and determined that we had structural damage and needed to obtain plans from an architect in order to proceed with the projectSolution: we hired an architect and completed the plans.Lesson learned:do a better job submitting permit applications, we believe we could have avoided the physical inspection had the permit application been submitted correctly the first time around. 

I'm looking for a architect in the fort Meyers Florida area lee county. some one that knows building and zoning.  

Looking for recommendations for an architect to submit a drawing plan to DCRA, because it's already a bedroom (I think).

I'd get with an Architect and have a set of plans started, then you can hand these off to a GC and have him start putting together a budget number for you.

i want to thank everyone for their thoughtf replies, I’m in the midst of getting ahold of architects and engineers.

I’d work with a professional on this (a trusted architect, a construction/ project manager, etc)

Got the Architect schedule for next week, going to some moves!

If you replace the pine with those tall upright bushes, realize they only look best when they are regularly cut.In other words, think about the budget for having a gardening service trim them on a regular basis unless it's your thing to cut bushes.Also before any big scale redo outside on such a fine looking home, it might be wise to talk to a local landscape architect about the whole lot, front and back.Good Luck!

You can talk to an architect to see what they say.