Re: ADs. There is a little “no fly” info box at the bottom. It is greatly helpful in identifying why certain elements won’t make it. However, you can still get in trouble around the edges - Wellingtons with 4K lb bombs might technically have the range until one small in week event means they don’t, or they run out of miles, or their airbase is under supplied. As for legal ground attacks - if you only targeted say, railyards, and then it didn’t work but did in city mode...that’s a bug worth reporting. But it could be something simpler, like bad recon giving a false picture of damage that then scrubbed the mission. Or any number of other AD canceling conditions (tried to fly on D2, minimum weather poor, but the path clips a terrible weather hex...).
As for Italian LW. It’s just not there to fight you with the historical set. Your losses are probably going to be flak based, with the odd GS counter. As of mid ‘43, Zitadelle has stripped the Italian Theater LW, and it only got worse. By spring of ‘44 there are less than 150 fighters (Paper strength) providing coverage to the whole theater. By the end of ‘44, less than 50. The AI may be playing cagey, but it typically doesn’t mind bleeding the LW - it probably just doesn’t have much to play with. If you want to give it the freedom to move stuff around, try the GC. Then it might move additional firepower into Italy.