Sounds a lot like us.....we cruised quite a lot the past few years and then bam, baby came along. That didn't stop us from cruising though. Our daughter was 15 months on our Harmony cruise this past February and she loved it!!
1. We brought an umbrella stroller but didn't use it much....only while walking around San Juan pretty much.
2. We did the Windjammer pretty much every meal except the 3 dinners we had at Jamie's.....they're super toddler friendly in there and even made special toddler meals.
4. No, but only because my parents came with us in an adjoining balcony room.
5. Just packed a whole bunch of clothes for the toddler....they don't take up much room in the luggage
6. You'll have a blast!!! Quite a lot of the staff have kids that they've left behind so they'll all be super friendly and accommodating.
We booked our next cruise on the ship for February 2020 and we just had to add our now 3 month old to the reservation.....she was quite the surprise lol. So in Feb 2020 we'll have a 27 month old and a 6 month old on board.