Your rambler looks great, what is the bar tape?
Did you chop the steerer? I would have thought they’d come with a longer steerer. I’d recommend https://bikeinsights.com/compare if you want to check stack height of frames before you buy, you can compare them against bikes you have that fit. What size frame is it and how tall are you?
Annoying that your tyres don’t quite fit although it does say on the Stooge website;
Worth mentioning also, not all tyres are created equal, so its probably true to say that not every 2.8 and 2.6 will fit.
I’m planning on getting a Rambler-alike frame made for me soon, I’ll probably go for 27.5 x 2.4 F and R.