Hi Maddie,
I've been in your boat. In a nutshell, if an obstruction resolves itself within a few days (hospital, fluids, pain meds, etc.), there is no need for emergent surgery. If it doesn't resolve on it's own, then there really is no other option. To your question, when is it time for surgery? Well, that's really up to you with some guidance from your surgeon. I had 5 obstructions due to adhesions in less than 2 years with hospital stays as short as 1 night up to a full week. When the 6th one happened, things were not improving at all after a week, so we went forward with surgery.
The advice from the surgeon that I had at the time was that we should have done it after the first 3 or so to avoid the really serious one that required the emergency surgery. Honestly, if I had to do it over, I don't think I would have done it sooner as the others were manageable and it kept me out of the OR longer. Who wants surgery after all the surgery we've had, right? Who knows though...having surgery when you are healthy and strong is also a heck of a lot easier! You can tolerate everything better, you're back on your feet sooner, and you can actually PLAN to be out of work and plan for the life event.
And lastly, to your question about how long to be home to recuperate...I've run the full spectrum. I've had a couple instances where I went into the hospital on Friday and was back to work feeling good by Tuesday. I've also had some that have had major lingering effects where I was functional, but things were just "off" for weeks. In those cases, the adhesions were probably still there causing some partial obstruction issues, but not causing enough issues where you can't eat and drink.
Not sure if any of that information helped you, but that was my story. I had surgery in March of 2015 and haven't had any issues since. 6 months obstruction free has been pretty nice!