All that to save $130 (and then you've got CAI hotel and taxi costs)? Or am I missing something here? And you're not going to do much sightseeing between 2000-0800.....

But if you do make the stopover then lots to see and do for a day or two. No more risky for someone frum than anyone else, IMHO, assuming you look "normal" - if you've got the Shemoneh Begodim then that might be different ;-)

Just keep you head down - so perhaps don't go on a day when we're not saying Tachanun? ;-)