Great photos Tim, and your analysis is spot on. The edges of buildings do create turbulent air, that especially if it is dry where you are currently, can be difficult, compounded more so if it is hot and the odor plumes.
That last photo has some really nice dense foliage which will be good to work in later. It will also get Molly used to pushing through, rooting, working with obstacles covering scent, which may be the case on some of the orchards you may visit. Not everyone mows their orchards. It also has a couple of nice (relatively) barren spots that will change scent flow, as well as the trees. Nice.
A bit hard to tell from the photo, but are those young Beech or maple (acer) trees?
Ask Dr. Thomas, but Beech in your area are known for being excellent hosts for summer truffles, so just FYI. Granted, they are not in a thicket there, so I’m not overly concerned, but I’ll ask him as well. It looks like an oak of some kind on the left in the 3rd photo, yes? Not overly concerned by that either, but just things to be aware of.
Do note the cement areas, if not using boxes, (and when dry especially) will prove more difficult for searches, as there is very little for scent to cling to. Those are some nice large areas you can expand into, with decently defined edges to set boundaries. They look good… And good instincts on approaching from different angles.