First your questions, then my lightning story.

There can be many strikes associated with the main bolt.
Many cloud-to-ground lightning flashes have forked or multiple attachment points to earth. Tests carried out in the US and Japan verify this finding in at least half of negative flashes and more than 70% of positive flashes. Many lightning detectors cannot acquire accurate information about these multiple ground lightning attachments.

Source: Termination of Multiple Stroke Flashes Observed by Electro- Magnetic Field: 1998, Ishii, et al. Proceedings 1998 Int'l Lightning Protection Conference, Birmingham UK, Sept. 1998.

Lightning Can Spread out Some 60 Feet After Striking Earth.
Radial horizontal arcing has been measured at least 20 m. from the point where lightning hits ground. Depending on soils characteristics, safe conditions for people and equipment near lightning termination points (ground rods) may need to be re-evaluated.

Source: 1993 Triggered Lightning Test Program: Environments Within 20 meters of the Lightning Channel and Small Are Temporary Protection Concepts: 1993, SAND94-0311, Sandia Natl Lab, Albuquerque NM.

Your question is not easily answered except by saying, yes. All those things and the stories told here can affect the path lightning will take.

Now for my story.

A Senators house in Delaware was struck on the chimney flashing. The path taken was down the flashing to the top floor fireplace where it transitioned down the flexible gas starter line. Under the kitchen floor (Inaccessible) the path jumped from the flexible gas line about 1/4 inch to a metal HVAC duct where it dissapated to ground. However, when it arced from the gas line to the duct it blew a pinhole in the gas line. Luckly it ignited the gas stream and started a concealed fire. The home started filling with smoke. When firefighters arrived no source of smoke could be detected. Using IR camera they found a hot spot under the kitched floor. A hole was cut into the floor and active burning was discovered and extinguished (gas line turned off as well). Had the gas not been ignited this would have probably been mistaken for a terriost act since the interstitial space would have filled and the ultimate ignition would have blown the house apart, along with the Senators wife. The pinhole in the gas line may have never been discovered.
That's one of my lightning stories.