>>182818010,000 hours in mspaint
the small box with the arrow represents how much back/up you could go to still be within reason.
the line through the headtube is the retard line where you could pull a meme fit with meme bars back to if you wanted to ruin the bike but not ruin it within the scope of ruining it. Don't do that though.
I strongly suggest you keep a quill stem. It's a cinelli front end right? 26.4? Be careful. Don't spread a 26 clamp for those bars or overtighten the stem for 26 bars without shimming.
Finding shorter/shallower 26 bars is probably the key here.
You might want a slightly shorter quill stem.
If you want bars at saddle height which imo is not necesserily bad then you want a dirt drop stem, they look better than technomics, or, you could try to get some 25.4 road bars and that opens up a tonne of mtb stems.
I really do think bars at saddle height with drops makes sense it just encourages you to use the drops more.
The crux of how that bike handles with less reach and or a higher front end is whether it's scary descending a big hill.