I currently have a 586, a CP88, a CP99 and a C225.
I much prefer the feel in the hand of the semi-auto style guns. And I dislike rubber grips, and finger grooves, which the 586 has both of.
But the 586 has two more shots per clip, better trigger (especially in DA but often in SA), better sights, very good build quality, and better accuracy.
Of the semi-auto lookalikes, you'll get differing opinions, but the CP88 tends to get the most plaudits.
The 99 fits the hand very well, but the sights are crude to the point of stupidity, and their adjustments are fiddly; the DA trigger is usually pretty awful (the SA is pretty good).
C225 is oddly appealing to me, but as a shooting proposition the CP88 is better (same sights, worse trigger in both modes, 1/2" shorter barrel so noiser and less powerful).
Less experience with the 1911 and Beretta. The 1911 ought to be a nice gun, but I have a mental block about a 1911 with a DA trigger. The Beretta probably is too, but I've never rated the real gun, and it is a big old lump set alongside, say, a CP88.
So, buy either a 5/686 or a CP88. Then wait and buy the other one. When you get bored, buy something else. But do NOT sell the 586/CP88, because you'll regret it. That's my advice.