My DS just turned 4-months and because I will be flying by myself, I thought I should plan early. I need all the tips/advise you all have. It is a 10 day trip and the first 4 days is sort of for work, DH is joining us on the 6th or 7th day and is flying with us on the way back. I decided to take DS with me since with his work, he can't take care of him by himself for that long, and we have no family nearby, plus I plan to still be breastfeeding by then. I already have childcare arranged where we are going, my friends mom who is watching her DD will be watching him at her house.
We flew with DS when he was 3 months old and he was awesome. He cried getting on the plane but slept the entire way on all 4 flights! He will be just over 6 months for this next big trip and I am a little terrified at the thought of it. Last time he carried him in the carseat/stroller through the airport, but I don't think I can manage to take all that plus another luggage by myself. I have thought about just checking in the stroller and buying a convertible seat and getting it shipped to where we are going. Since DH will be with us on the way back, there will be more hands for more stuff then. Does this seem like a good idea? I have an ergo but I have only used once and he hated it (but possibly because he was still tiny back then). My plan is to travel with him with the ergo and just a diaper bag. Have the stroller and the rest of our stuff in a luggage checked-in.
Also, the least amount of driving will involve 3 flights (2 stops)


to get a non-stop flight, it will involve driving ~4 hrs to a major airport, followed by non-stop flight and then driving 1.5 hrs to our final destination. DH can make the first 4 hr drive but we will most likely be leaving the house at 4am

I am really worried about doing this alone but this trip needs to happen and cannot be postponed (sorry to be vague with this part). DH just can't take this specific time off and it was the only time that worked with the people I have to "meet" with. I don't know what to do with the sleeping in the hotel part yet. I am not sure if I should but a cheap pack-and play.
If you have travelled alone with a baby before, what made your trip easier? TIA
Re: help me plan a work/fun trip and travel with a 6-month old