Hello guys, firstly I want to apologize for creating a big post without taking proper care of my setup, I guess it was a power related issue at all. I`ve managed to boot all the images (current stables, and developers one).
I`m posting this from the Orange Pi Win Plus with the current desktop stable image (Armbian_5.41_Orangepiwin_Ubuntu_xenial_default_3.10.107_desktop.img) and it`s working great. I`ll do more testings and share my finds with you.
I`ll use the server version, but wanted to try the desktop image.
My problem was inside the power jack plug, it was someway loose inside and thus not offering proper contact with the central pin of jack (plus) off the board. The connection between the plug and the board was pretty fit so I didn`t thought that this would be the origin of my issue. I discovered this because I decided to power the board using some testing logic clamps I have laying around instead of the plug itself and then the board booted flawlessly with all the images and with all micro sd cards I have.
I thought the problem would be a bad solder joint on the plug itself, but in fact it was a problem inside the jack`s barrel. I crack it open to see what was going on and the metal connection inside the barrel was broken and barely making contact, it was only "working" because when I plugged it onto the board the pressure between the metal parts and the central pin of the board provided some contact.