I don't think ORL is good enough to be signing a UFA and have a couple years of tank in them TBH. Same with MIL. And I don't see Lowry saying yes to either because they just aren't winning.
Both teams, especially Orlando, have a lot of really good young talent, and both have cap room.
Orlando is a lot more attractive as a city obviously, and their core young talent(Oladipo, Harris, Harkless, Vucevic) is better than Milwaukees. Plus they have Afflalo, who is one of the best players at his position. With another lottery pick, and players developing this season with a lot of minutes as mentioned above, they're really only a few veteran players away from being really really good IMO.