Honda Ruckus or Honda Monkey ???

the ruckus is slow. like S.L.O.W. slow. and the brakes are hot garbage. however, everything under the sun exists for upgrades, if you're into that sort of thing. myself, i'd skip all that and go straight to a zuma 50 2T swap and call it done-- with a better front fork.

speaking of zumas... for what it sounds like you want to do, the zuma 50 2T would be perfect. great bike in stock form, even better with a kit and a pipe. equally at home on the pavement and fire roads. good chassis, great brakes. tons of aftermarket support. cheap used.

if you want something that is super capable, the honda ADV 150 is a great choice and if you like shifting the grom as well. both a spendy, but really great bikes. same goes for the zuma 125, albeit you don't pay the used honda tax.

don't discount the piaggio typhoon. a great bike, but again can be a little spendy. plastics can be a little problematic, but all the hard parts cross over to vespa. used they can be a real bargain.

avoid anything aprilia no matter how cheap.