I am a real all or nothing person. When I made the decision to lose weight - I changed EVERYTHING up. I know that does not work for everyone, but for me it was the only way. I couldn't leave the door open for any missteps. But again, that's just me. You need to find what works for you. There's no one "right" way to do this. Ha, if there only were.
Also, when I did make the decision to lose the weight, I was real anxious to do so. I had SOOO many bad habits in place and I felt it was just best to replace them all, right off the bat - and get rid of the weight.
I did set myself up for success though, but in different ways. Well actually for me, changing everything WAS setting myself up for success. Some other things that got me on the right track - I started a journal, something I never, ever did before. I wrote in there all the reasons why I wanted to lose the weight and referred to it often. I tracked my calories - I was too nervous to overspend them and more importantly - forced portion control. I rid the house of ALL junk. I ADDED in tons and tons of veggies and other healthy, low calorie items. I planned/mapped out my food in advance. I couldn't leave my food to "chance". Too risky. I took healthy snacks and food with me.
Of course my plan and eating has evolved as I got further and further into my new healthy lifestyle. And of course my exercise has increased as I got smaller and more fit.
All your plans sound exciting!!! I look forward to hearing more from you as you embark on a thrilling journey towards good health. All the best.