I'm no expert on this but if it were me I'd pay more for more provenance, or at least a statement from the former owner as previously suggested.
Wheeled street-drivers... a current title and registration is worth money because it's usually easier to transfer ownership and get a license. An expired registration is not much worse. Automotive makes like Ford, Cadillac, Buick, should be more friendly to DMVs.
Some wheeled vehicles and many tracked vehicles were not made by companies that are familiar to state DMVs so could cause more of a hiccup. Companies like Baldwin Locomotive, Detroit Tank Arsenal, FMC, Oshkosh, Sauer, MAN. So expect more trouble. Shouldn't be that way, but computers usually make things black or white.
Military Vehicle Collectors of California
44 Ford M20 (A1 Tactical Hot Tub)
41 Indian 640
BSA folding bikes