I'd suggest taking 30 seconds out of your busy day and doing a search in this forum. The EXACT question has been asked and answered 5 billion times.  Just on the first page in this forum alone there is a 2 page thread dealing with this.
Since apparently the search button option is turned off on your computer the answer to your questions is yes tow in OD. Only turn off OD if the trans is hunting between gears trying to maintain speed. With that HUGE trailer you're pulling you'll be fine.
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99 F250 PSD 4x4, 5" DIY exhaust, CCV mod, DIY intake, PMT1 with DP Tuner chip (stock/40/80/120), BTS VB, Suncoast Extreme Trans with SD43 converter, FASS fuel system.
Trail Rig: 95 Ranger on Kingpin D60/14 bolt/D&D Doubler.
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