The answer would appear to be you do not need to examine two characters, looking at the first character only is sufficient for implementing If-Range
.
If you look at Apache HTTP Server implementation you can see that it only examines the first character (http_protocol.c, line 477 at time of writing).
if (if_range[0] == '"') {
I think the slightly misleading wording of the text can be explained by looking at an earlier version of the HTTP 1.1 specification (RFC2616) where it says:
The server can distinguish between a valid HTTP-date and any form of
entity-tag by examining no more than two characters.
The older statement is not wrong but not immediately relevant to If-Range where only strong ETags are permissible.
I expect the RFC7233 form of the text was an attempt to make the previous text clearer but unfortunately on this occasion it didn't achieve the clarity it sought.