Auto Racing: oil cooler, hotrod magazine, rear wheel horsepower

Question
Would it be worth the money to invest in an oil cooler, and a transmission fluid cooler? Would i improve in efficiency/power/gas mileage on my small block 350 with auto TH350 trans? also, i would like more power out of the 350, so i was thinking about a small super charger, like the holley 144 power charger. Would i have problems like streetability if i put that supercharger on, or would it just be a simple increase in power?  

Answer
HI ERIK. COOLERS AREN'T A BAD IDEA  BUT IN THIS CASE I'D RATHER SPEND THAT MONEY ON REPLACING ALL OF THE CAR'S LUBRICANTS WITH  FULL SYNTHETIC OILS(RED LINE,MOBIL1,SYNTEC ETC.) ,A MAGAZINE ARTICLE ON JUST SUCH A REPLACEMENT  SHOWED A BEFORE AND AFTER DYNO TEST  AND THE CAR SHOWED 10 MORE HONEST REAR WHEEL HORSEPOWER!THE SYNTHETICS ARE MORE STABLE AT TEMPERATURE EXTREMES AND PREVENT ENGINE WEAR AMONG OTHER BENEFITS .THE COOLERS WOULD SHOW NO HP INCREASE AND MOST STREET USE WOULD NOT WARRANT THEM .THE SUPERCHARGER IS A GOOD IDEA,THERE WOULD BE A RATHER LARGE HORSEPOWER INCREASE WITH FEW PROBLEMS ,ONE OF THE FIRST HOTROD MAGAZINE POWER TOURS HAD A CAR ('69 CAMARO I BELIEVE)THAT TRAVELED ACROSS THE  COUNTRY SEVERAL TIMES WITH NO DIFFICULTY OR RELIABILITY ISSUES. YOU MAY LIKE THE WHINE THE BLOWER HAS TOO . THANKS AND GOOD LUCK.  JOHN MAZIO