Depending on the 60 hour mark I'd wait for that first.
After 2days 12 hours (and up to about 15 minutes after) the dweller will encounter the National Guard Depot. It has a (from hearsay) 1/10 chance of a legendary drop. So if you want to take a chance, and why wouldn't you, wait for that.
Beware though, that mostly it will be something like "120 xp" for the reward of finding it.....
Best chance to get gear is to have a lot of explorers. Before the patch I had a rotation of 35 level 50 Dwellers with maxed SPECIAL, I would send them out with 25 stims and 5 RadAway. Once the stims where gone, i would recall them... Once they came back, I would sell off the crap and keep the good stuff... and send them right back out. Keeping this rotation going, I would get good loot. I have 6 power armor, a fat man, a couple of rocket launchers... etc. My whole vault is equiped with weapons with base 11 damage or higher (I sell every thing lower than that).
After the patch I restructured everything to compensate for the DC attacks. I am now working my way back to that rotation again... up to 24 Dwellers in the rotation now.
Yeah, essentially as Pj3r says, but since the newly discovered 75:00hr Mr. Handy event, probably you should go for that event instead of the 60:00h National Depot.
Currently, the only confirmed result is caps... but taking into acount that it's a 75h event, a success could possibly mean to get a Mr. Handy for your vault.
And as Mustangnut says, a wanderer rotation is the best choice later on, since your main source for items will be the hourly and fixed timed events (mainly for iOS users, android ones will still take some time to get several dwellers with full SPECIAL values, and enough stims for everyone)
Still, you do not need to go with 10 SPECIAL values, legendary dwellers have high enough values to get decent ittems from scratch. Currently, on my newest vault (a little more than 50 dwellers, so I have all training rooms enabled), my playstyle is to send my best legendary dwellers suited for wandering (a Preston and a Bittercup) and a decently trained vault dweller (high Str, 10 End, decent Luck) to the wastes on mondays, with 25Stim/5Rad, then recall them on wednesdays after Depot or Handy, checking every few hours, when I connect, to see how they fare in case they require an emergency recovery. This way I have them back on friday and spend the weekend training them while I send some "crappy" dwellers for some caps and easy leveling (for wanderers, I go first for 10E so almost all radiation is nullified, then I'm currently focusing on Luck; after that, I'll probably level up their other stats evenly, starting with the lowest ones).