Hi,
This question might be more appropriate for second time moms, because I'm asking a specific question about a double stroller. But I got such great information about the nursery decals, which I ordered yesterday so YAY, that I figured it was worth asking my stroller question on here, too.
First of all, my husband insists that I don't need another stroller. He might be right. Here is what I have and whether it worked for me, just so you can get some background
1) chicco travel system and car seats--that's the stroller I use now that he's older but I didn't like it for the infant carrier
2) snap and go from when DS was an infant-- loved this and used it primarily until DS grew out of the car seat.
3) BOB single jogging stroller-- hated it, too bulky to get in and out of the car. I really need to sell this one on craigslist or something.
4) an inherited double stroller, some sort of gracco, that is really LONG because it seems like it's for two toddlers? It seems pretty old and dated... I haven't used it yet but I don't think I'll like it. DH said the car seat doesn't seem to "lock" in well either.
5) several umbrella strollers (in grandmas car, DHs car, etc.
So what I WANT is a compact sit and stand type, something that isn't bulky to get out of the car and would be good for my infant alone AND when my 3.5 year old is with us. I seem to want the ease of a single stroller but have it fit two kids. Too much to ask, perhaps. My cousin has a Phil and teds that she loves, but it seems expensive and maybe better for kids who are closer in age than mine. I don't want to spend too much, maybe around $100-$150 or something. I can get it used, but I also have registry completion at Target combined with redcard and pharmacy discount, so it's a huge plus if I can buy it at target--25% off, almost. Any suggestions or links would be AWESOME. Thanks for reading this much!
TTCAL Siggy Challenge: "He's my favorite. His birthday is the same as mine almost"

Missing my little one lost at 9 weeks on 2.24.13. brokenhearted but not broken...
d&c 5/21/13... Still Healing, Still Standing...
MMC discovered 10/2/2013, TWINS... d&c 10/7/2013. I still miss you, little ones.
Surgery December 2013 to remove a 10+cm fibroid... Open myomectomy. Benched for 3-9 months...
Will TTC summer Summer 2014 we hope!
Dear God, Since I couldn't hold my little one in my lap and tell him about you, could you hold him in your lap and tell him about me?
PgAL and PAL always welcome...
Re: Stroller Question
TTCAL Siggy Challenge: "He's my favorite. His birthday is the same as mine almost"
Missing my little one lost at 9 weeks on 2.24.13. brokenhearted but not broken...
d&c 5/21/13... Still Healing, Still Standing...
MMC discovered 10/2/2013, TWINS... d&c 10/7/2013. I still miss you, little ones.
Surgery December 2013 to remove a 10+cm fibroid... Open myomectomy. Benched for 3-9 months...
Will TTC summer Summer 2014 we hope!
Dear God, Since I couldn't hold my little one in my lap and tell him about you, could you hold him in your lap and tell him about me?
PgAL and PAL always welcome...Honestly, I don't many double strollers that are going to be light and easy to deal with when you are trying to stick an older kid in it. I think the sit n stand might be your best option. You might also look into the skate boards/scooters that are made to clip onto the back of single strollers. They look inconvenient and in the way of mom trying to push the stroller, but it might be another option.
ds#1 and ds#2 are 4.5 years apart so I bought the sit to stand stroller and used it maybe 3 times. I hated it. It was long and the infant seat was in the front which seemed like a mile away when I was pushing it.
now that #2 and #3 are going to be less than 2.5 year apart, I bought the countours optima tandem stroller. DH thinks it will once again be a complete waste, but I wanted to try it and see. ds#2 HATE riding in the stroller and I'll probably end up just pushing around the baby, but if that happens I'll just go back to our single stroller and let the others walk.
~after 34 cycles we finally got our 2nd little bundle of joy~

My IF blog
How about push chair then?
OP, I'd suggest a buggy board type of attachment since your dc is older. My 4 year old dd hasn't used a stroller since she was about 18 months, she will walk for miles and miles. I like letting her walk because it teaches her discipline and well,she gets to move around. However, I got the buggy board attachment because it seems 'cool' and well, it's an attachment not a whole new seat. I figured, handling two kids might be an adjustment and I could use the little help of having her next to me if I'm alone with her. Alternatively, could you wear the baby and put your son in the stroller if he wanted to use it on some days?
Per https://carseatblog.com/28339/peg-perego-primo-viaggio-4-35-rear-facing-infant-carseat-review/
The Primo Viaggio 4-35 may be used with most recent Peg strollers, including the Book, Book Plus, Book Pop-Up, Switch Four, Duette and Triplette, Vela Easy Drive, Pliko Four, Pliko P3, Pliko Switch, Aria Twin 60-40, Si, Uno and some other older Peg strollers. It is NOT compatible with the Pliko Mini or Skate System strollers. Unfortunately, adapters for other brand strollers are not readily available at this time, but some are expected this fall.
https://www.babyjogger.com/uploads/CSA-Guide.pdf
I don't need five do I? Someone tell me I don't need five... *FTM panic*
https://www.babyjogger.com/product/city-select/
Check out the configuration guide.
For now, I might just hold off and see if I miss having a double... I keep the idea of the skateboard things, but he's so tall that on our stroller we can't get the handlebars out of the way... The only places I will NEED a stroller for 2 are the mall or or long walks, and maybe I'll just have to take DH along!
Thanks again for all the helpful responses!
TTCAL Siggy Challenge: "He's my favorite. His birthday is the same as mine almost"
Missing my little one lost at 9 weeks on 2.24.13. brokenhearted but not broken...
d&c 5/21/13... Still Healing, Still Standing...
MMC discovered 10/2/2013, TWINS... d&c 10/7/2013. I still miss you, little ones.
Surgery December 2013 to remove a 10+cm fibroid... Open myomectomy. Benched for 3-9 months...
Will TTC summer Summer 2014 we hope!
Dear God, Since I couldn't hold my little one in my lap and tell him about you, could you hold him in your lap and tell him about me?
PgAL and PAL always welcome...I personally probably wouldn't get a double stroller if I only hand a 3.5 yr old (I also have a toddler) but my kids not a runner, so you obviously need to do what's safest. Just sell the ones you don't use.