First, some background information: I am a medium height (5'9") in-shape male with an above average neck size (16") for my body (39" chest; 32" waist) Consequently, throughout my life I have found it very difficult to find quality ready-to-wear dress shirts that fit me properly. Most of the shirts that fit my neck are too long in the sleeve and balloon in the midsection, and the shirts that do fit me properly in the sleeve and waist are often still too long for my taste. Thus, I have come to the conclusion that ordering some made-to-measure dress shirts will solve my woes.
My biggest question is: where from? I have read some threads about various M2M online shops such as Modern Tailor and Proper Cloth and they seem like a good deal for the price, but I am hesitant because I'm not sure I will get the fit I want from just inputting numbers into the site and not having a proper tailor measure me. My other option is going somewhere locally and having a proper fitting. One huge plus about that is I live in northern Italy, and I'm only a short, cheap train ride from both Venizia and Milano, where I'm sure world-class tailors and shops abound. The downside of that is I'm in the US Army, and don't have a ridiculous amount of money to spend on custom clothing, so I'm not sure if I would be able to afford any of the high-end shops around here. I'm willing to pay $250 per shirt if the quality and fit is right, but that would be straining my budget and I would prefer to stay under $200.
So should I try my luck with the online shops or should I seek out a quality local shop where I live? Does anyone have any specific recommendations for online shops? Does anyone have any recommendations for quality brick and mortar shops and tailors in Italy I could try that would fit within my budget?