I appreciate you going through this. Being a commuting single parent that has 3 cats and a dog (albeit a very small, mostly indoors chihuahua) and of course. a small human can often be a challenge. It’s an adjustment and takes time. Remembering that most requirements demand logic and being a parent (pet or child) demands heart. It’s a different kind of coping. You’re worried Winston won’t adjust, but remember, he’s likely more adaptable than you think. All of my pets have adapted well to my crazy life. Dog and kid included :)

Give him a break. I guarantee you wouldn't regret it in the long run.

Life isn't easy, dude.

When we first got Sponge, I felt the same way. You expect it to be a lot of work, but it's like having an infant. I had those same fears, felt overwhelmed, and spent several days in tears – like, the whole day, just crying at how hard it was and how stuck I was.

But over time, it gets better. You both start to understand each other better, and it's easier to manage. Early on, I couldn't leave the house for more than 3 hours with the dog crated, and even that felt like really pushing it. Now, if I had to, I could leave him for 8 hours or more loose in the house with food out on every table top.

Most of the problems you mentioned are fairly easily correctable, and in solving those you'll probably find the big problem to be a lot smaller than it seems now.

The beginning is going to be stressful for anyone taking in a new dog, and it probably won't become un-stressful within 3 or 4 days but it will get better every week.

If I were you, I'd take a little time to see how well the dog learns – if he's a quick study and can pick up new routines / behaviours without a lot of struggle, you might start to feel more optimistic and enthusiastic about the situation. When the dog starts to understand you and what you want from him, there's a whole new bond between the two of you that makes the rest of it seem less invasive.

If he doesn't make much progress, and it looks like it's going to be more of a challenge than you can undertake on your own, re-homing would be a fair option. I definitely wouldn't judge you for it, it's a major change.

Whatever you end up doing, it will be good life experience.