I don't really now of any semi auto gun that is all that hard to field strip for cleaning of the primary parts.
But if you're going to get all fussy and want to totally clean out the action each time then you'll want to go with removing the grips and just flushing the action with a powder solvent. Otherwise you'll do more harm in the long run than you do good.
Of all the guns I have the 1911 is actually one of the more time consuming ones to strip and re-assemble. Note I didn't say harder or worse. It's neither. But it does have a few more parts and steps that need to be done compared to most others.
For "fun" I'd say go with a 9mm just because you'll buy more ammo per buck. And what's more fun than shooting more ammo for the same cost?
As for which 9mm to get I won't even go there. Surely there must be some sort of rental shooting range in your area? Head over and invest the bucks it costs to try a bunch of options out. There'll be one or three that seem to fit your hands better and have the right look. In particular pay attention to the style of gun. The big two are hammer vs striker fired. Then there's polymer vs all metal. For a range fun toy the all metal seem to find more fans. But you'll need to find that out for yourself.
The big thing is that if you ask us which gun to buy we'll just tell you to buy the same ones we like. It'll be YOUR gun so step up and try a few out and decide for yourself.
PS; When you get to the Rent-A-Gun range be sure to try out a full size style revolver in .38Spl as well. You may just find that you like wheelguns over semi autos. I never thought I'd be a revolver fan until I tried one. Now they outnumber my semis in my collection... Actually they were about even until I discovered how much fun shooting black powder is. THEN the revolvers took over....
