Hi Mike and Jenny!
It was a pleasure getting to meet with you on Monday and talk through options for your Dining Room and lifestyle needs for your growing family! I have compiled the below options for dining tables, chairs, and barstools for your review.
I wanted to point out that your current table measures 31-1/2" wide. Tables being made now a days are starting at approximately 40" wide. Since this will be a substantial difference, I suggest you measure out with blue painters table the dimension of any table you are leaning towards so that you can visually accept the width before purchasing. Also, please note that all the table and chair options I preposed below are interchangeable. Chairs are trendy and undergo more ware and tare than a table typically does. Economically it may make more sense to purchase the chairs at a retail store (Target, Walmart, Stein Mart) where you can test them in person (super important for chairs!) and take advantage of deep retail brick and mortar discounts.
In terms of storage, I LOVE your current sitting area with the side chair and table! I suggest getting a second chair to match the existing which will add to your current sitting area. Your everyday table would be 6 chairs total (2 on each side and 1 at each side of the table). When entertaining, you would add the leaf in and move the everyday chairs that are at the end of the table to be 3rd chair on each side. Then, you could bring the sitting area chairs in for the head of the table on each side).
Lastly, please keep in mind the suggestion we spoke about regarding one side as a bench-this is great for kids when entertaining the extended family or friends and will help on the overall budget. When the bench is not in use, you could place it behind the back facing bar- sofa for additional seating and a quaint area for staging your favorite pillows and throws.