With a good custom burnt chip you can have both. You can run something along the lines of a 230cc Hybrid and have a detuned tow program to keep the smoke down and EGTs under control. Have a fun program burned to use the fuel those hybrids will produce. 180cc's are great for towing and not bad for fast, but Jody can do a lot to make big injectors work well towing. You might want to give the tuner of your choice a call and ask them as well. I would go with single shots to make the most use out of the HPOP
As for turbo, are you talking about swapping a wheel onto your existing turbo? The GTP38R is a ball bearing turbo with a 88mm wheel. They spool very quickly and work pretty well all around. Some don't like it, most do for mild tow/street rigs. A lot of guys like the TN drop-in as well, however lately there have been some guys have trouble with them as well.
If that is an early 99 you have and you haven't converted to SD parts yet I would look into either an H2E or a D66 which is a drop-in. D66 can be had from Beans Diesel Performance.