WOW I just took at look on Google Maps streetview of Harbor Island and what i saw taken in 2014 if I'm correct looks great!
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Harbor Island itself is a very nice area. Have some long-time friends of my family who've lived there for 40+ years and wouldn't live anywhere else. It's isolated and surrounded by canals, of course, and is a close-knit little community with neighbors who care.
The rest of the neighborhood north pf the canals has certainly deteriorated from the time when much of my family lived there [[I still have a few relatives in the area), but there is also still a lot of nice housing stock and folks trying their best too. It's really a street-by-street and block-by-block thing. Lakewood, the street that you drive on to get to/from Harbor Island, is probably the best street in that neighborhood.
Riverside is nice as are parts of Newport, Dickerson/Lenox is a breeze all new housing, Scripts is cool, parts of Piper and Marlborough [[sp) all have some beautiful homes. 4 riverfront and under maintained riverfront parks for jogging.
Why not try renting a condo on the northern tip of Grayhaven Island, they also have public/ private marinas in that compound. If security is an issue its actually triple gated and have round the clock security at the primary gate.
Has anyone parked in the nearby park and walked to Harbor Island? I have a friend who is a boater, I think he would enjoy seeing the area.