I think you need to assess how your LO handles deviations to the routine. My DD wasn't very flexible when we deviated from our routine. It would take her several days - sometimes weeks - to get back on track if she missed even one nap! So, I stayed home and made sure to give her the routine she needed. I spent a lot of time unable to go out, but it was a sacrifice that I was willing to make because when she was unhappy and unable to go down for naps, I was miserable! And it took a lot of pu/pd to get her back on track! If your LO is able to adjust easily then I'd say you could probably manage it well. Maybe in a week or two, once he is really used to the 4 hour EASY you could try going out and see how he adjusts? But be careful, because my experience taught me that even once can really mess things up!! Good luck!