Len, if you were shooting some portraits, where would you shoot?
I try to find inspiration from the person.
I like to go to their favourite park, building, or to their favoured type of building (old, new, shiny, glass, etc)..
I love to use historic buildings, like the old hospital at Nielsen Park that NPWS uses as offices. (you would need a licence to do work there with a model - see the NPWS website for more information)
Sometimes I go totally natural with some, others a combination and some just industrial places.
If it is a commercial shoot I take 3 - 4 hours and do three or four locations. Each location gets a clothing change. Saving the best till last. For when they are relaxed I will probably get the best shots at the end. Though this hasn't always been the case.
I am looking for open shade to work in. Usually. If there is none (there always is some), I shoot with the sun behind the person and let their heads create their own.
Working in one spot often gives me inspiration for the next. Trying to find what works for them. So I have a list of possibles in my mind, all close by, so I can dip into my bag of possible locations and choose the next one based on my current feelings.
One vehicle so I can take them around.
In some instances they drive me to their favourite spots.
A rambling answer I know, but I hope it helps.