I see that there is one wall with the door plus the other with what appears to be a window with the oddball roof angle.It is hard to say how it will look.

Landlord shall maintain, and/or repair/replace the plumbing, heating, cooling, electrical systems, and the exterior walls and roof of the Property.

Remodeled interiorReplace roof

Would you have any major repair costs coming up (roof, AC)? 

Roof, swimming pool, interior, exterior, driveways, landscaping, etc.

If the LLC is an operating business..... lets say providing roofing services with annual revenues that are consistent or even better increase year after year for 10 years, lines of credit or other lending options might be available that aren't available for a new business. 

How are the major potential expenses of the house looking (AC, Roof, Plumbing, Electric)?

My main concerns about Florida include: Chinese Drywall (very toxic; found in older homes); HOA Restrictions; Lots of people/crowds; sinkholes (properties sinking into the ground); Red tide (dead fish found on beaches due to algae bloom); Homeowners Insurance costs (w/older roofs); Mold; Hurricanes/Flooding , New construction (not always built to quality)... these are the most common issues found in the Florida market.What zip codes would you recommend for a single family investment property under 300k to mitigate these concerns? 

For roof-mounted solar, you need a roof that is oriented well and gets good solar exposure in order to produce power.

The reason I am ok with that is because I just spent $140K and updated everything - electrical, plumbing, roof, HVAC, windows, etc. so costs should be minimal for a while.