Can I just offer the occupant money to leave without having to file a forcible entry and detainer?
Absolutely, in fact I suggest this as the first option. Consider offering the occupant a small amount of money to vacate. Perhaps the amount that you would be spending if you brought the forcible entry and detainer action. This agreement could be a win-win for both of you. You will save money, time and aggravation, perhaps the property will be in better condition and the occupant will receive some sorely needed moving cash. But beware the occupant that is just buying additional time and never intends on moving until the Sheriff is at his door.