"First, the guy told me that the FR replacement gearbox was not a good box"
This is mostly bull because the FR box is a good, improved, recirculating ball gearbox. Like all recirculating ball gears it has some hysteresis meaning that it has a dead band in the center that reduces driver road feel. It is typical of '60's automotive technology and is/was the type used in Shelby Mustangs of that era.
"because it would still make my steering difficult for the type of driving i want to do.:
Vintage racers are still driving cars with these kind of steering gearboxes. They have good road feel but not excellent.
"BTW, i want my car to be more like a weekend warrior and an occasional car i can drive to work without killing myself in turning the car or trying to get it to stop. Yes i would like performance out of it, but more of an occasional driver."
Flaming Rivers gearbox is a satisfactory answer to your problem.
"So what he proposed was that he could "rebuild" my stock one into a "powered" (power steering) box. He said it would run me about $250 for him to do that. Does that make any sense????"
No. Adding power steering of the kind he can do for $250 only gives you used power steering components off a same generation Mustang. It will have lighter forces but not better steering response.
" He also told me that if i went to the rack and pinion system that it would SIGNIFICANTLY depreciate the value of my car. I'm not trying to sell it or anything, but i figured it would keep its value strong enough with or without the rack."
Any retrofit carries the stigma of being a deviation from OEM design. It affects the authenticity of your classic car. OTOH, well designed retrofits can improve performance of your car in a manner never imagined by the original designers. Theres a percentage of future buyers that it would turn off, again theres a percentage of future buyers that it would turn on. Only you can decide what you want now and what you want in the future. Note that should you want a rack and pinion now but want originality you can save the removed parts for future conversion back to the OEM configuration, its not that big a deal.
"Now about the brakes, he told me he it would run me about $975 or something like that. I just looked on the Wilwood website and the closest thing i could find to the price you mentioned was the Medium Duty front brake kit, part number 140-4307-B for $517. Is this the kit you have? And if so, what other parts would i need so that i could "bolt" it up to my car. I dont know jack about brakes"
One of my associates said this about his '66 Mustang coupe and I quote, "We bought the Wilwood kit, and everything bolted up slick as can be...its so easy to change pads you wouldn't believe it. The only thing thats hard about it is forming the lines to get a good looking installation."
My advice is to read up about the Wilwood system. There are installation hiccups...you gotta have acceptable wheels/tires to get requisite clearances, etc. Wilwood is also not DOT approved so you'll be trusting the name and reputation of the company and not a government authority. If you think DOT sanctioning is crucial, then go with the SSS system. Theirs is a perfect replica of the original Ford brake system. Insofar as I know, it is DOT approved.
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