Depends on what you mean by succeed. I voted yes as I think if Microsoft launched a proper handheld gaming device they could break into the market and break even or even make a profit. However is that the level of success you were refering too?
I think a Microsoft handheld could probably capture about 20% of the market, taking share from both Nintendo and Sony. I think Nintendo would still come out in first, with Sony second and Microsoft third. But I would still consider it a success.
Of course Microsoft would need the same stellar first party software 360 recieves, meaning a new Halo for launch. Give it a good Gears spin-off a Forza title and some other hot properties at launch. I'm sure the handheld console would sell, also give it Live compatability with XBLA full catalogue of games availible on the new handheld day one.
I think Microsoft would have a fighting chance, of course their first entry into the handheld space would not topple Nintendo or Sony. But their second entry could possibly take second place and if Nintendo makes another big mistake heck MS could be looking at challenging them for first.
Of course the biggest hinderance to Microsoft's ability to take the console or handheld market is Japan. Japanese gamers just aren't interested in Microsoft's properties and consoles. So I think Microsoft would once again hit that road block!
But yes I think a handheld Xbox would be successful!