I like to set mine to "Stat, Check All CC" but then set the scan-delay on the trunked systems a bit longer (3000 ms or so) to catch the reply. I leave my conventional frequencies to under 1000 ms because the repeater hang-time is usually long enough to catch the reply with just the extra second.
Here in Kansas our state-wide interop system (KSICS) usually allows you to hear anywhere from 2 to 6 sites at the same time in about 2/3 of the state. Looking at the RR maps for SoDak, it appears your system is similarly spread out. By using the "Stat, Check All" option I definitely pick up more traffic.
The best thing to do is to try all three ways. The control is about 11 lines down in the TSYS programming if you are doing it by hand. Try ROAM for a week, then switch to STAT, YES and then STAT, NO. You can adjust the threshold values in ROAM also to see what works best.
I haven't messed with the Extended Settings that much yet, and truthfully "the perfect setting" for those are going to vary from system to system and scanner load to scanner load. Play with those too if you want. There is always the "IMPORTANT" button to reset them back to default settings if thing go wrong. I'm almost positive that Don didn't include a "self-destruct" feature in WIN500 anywhere, so there is nothing you can enter from the program that is going to break the scanner.
Just make sure you save your work files frequently and the default scanner load though!