Tip Simons, partner at Simons & Taylor Real Estate, is a deeply rooted resident of the Old Village. His connection is generational: his home on Bennett Street, built in 1809, has been in his family since 1935. Tip grew up visiting the house and always cherished the time spent there. In 1992, the property gained a bit of fame when the film Rich In Love was shot on site, and the family enjoyed watching parts of the movie being filmed right at home. After inheriting the property in 2006, Tip was able to spend more time there during the COVID pandemic. He completed renovations, added a deep-water dock, and placed a historic easement on the property, preserving 1.7 acres of open space. In his downtime, Tip enjoys the neighborhood's relaxed pace—walking to the Pitt Street Bridge, biking to Sullivan's Island, and participating in the "Creek Crawl" at Shem Creek. He continues the family tradition of hosting Thanksgiving at the historic home and loves the neighborhood's festive Halloween atmosphere. Tip appreciates the Old Village's enduring "small-town feel" and charm.

Ruby (Red Short-haired Dachshund) was 16.5 years old at the time of her feature. She's a very loyal and affectionate dog and easy to tote everywhere due to her small size, weighing in at just 7 pounds. A fun fact is that Ruby was born with dental issues and required braces as a puppy for a year to correct her bite to eat food properly. Since making the move from Colorado to Charleston with her mom, Robyn Lynn, Ruby has enjoyed the beaches of Charleston and walking and swimming in the tidal pool water.