I live and work in Ocean City. I also have an 8 year old and we practically live at Northsaide Park. Its one of the best amenities in OC and they Rec Dept. does a wonderful job of promoting activities year round! Montego Bay certainly isn't far away but there are other communities and buildings nearby as well that may be worth considering. You mentioned Ocean Pines....although I reside in Ocean City I find myself in Ocean Pines quite a bit. They have outdoor and indoor pools that we frequent, not to mention several parks. Although further from the beach, Ocean Pines does have the Ocean Pines Beach Club on 49th St. and the ocean, for residents only. Its a phenomenal perk. There are several more listings available in your price range there and could potentially offer much more value for your buck; bigger property, house vs. condo, etc. One thing I will say is that with 3 young kids you won't be at a lack of activities in this area. Regardless of where you are you will likely take advantage of the amenities in both areas. I hope this helps. If I can be of further assistance please contact me, email@example.com. Best of luck!