N4411 is almost certainly not the original registration for Bruce's 150F, and was probably assigned in 1997.

Cessna normally requested and received registration numbers in sequential "blocks", which often corresponded somewhat to the airframe serial number. For instance, Cessna 150 serial number 15062559 is a 150F registered as N8459G, and serial number 15062561 is a 150f registered as N8461G. Bruce's 150F is serial number 15062560, and was likely originally registered as N8460G, which is currently an unassigned registration number reserved by a Mr. James McDaniel.

TIP: At least on Cessnas, always check registration and serial numbers close to the subject production airplane for additional information suggesting registration changes, as these were almost always assigned in blocks of numbers. Why check? re-registering to a new N number can sometimes hide damage history, unless you know where to look!

I don't think that's the case with Bruce and N4411, as the aircraft was registered to him on 12/08/1997, and there is apparently no damage history in the database for N8460G. Although currently unassigned, any documented damage history in relation to N8460G should still appear in the database (but, it is possible that the more recent reservation of this number by Mr. McDaniel has now erased any prior history! Still, Google and other sources show no recorded history anywhere on the web.)

It is also likely the number N4411 in the SDR report is a typo, and was likely not the original registration on any Cessna 310! N4410 is a PT-17 biplane, and N4412 is a Phoebus sailplane.