Вопрос: Каким должно быть регулярное выражение для email по заданным условиям?

Лучший ответ: Можешь выбросить все эти свои собственно выдуманные правил для email, потому что существует RFC 822,который определяет как в действительности должны выглядеть email-адреса.
Нормальные программисты никогда не проверяют email по regexp
https://en.wikipedia.org/wiki/Email_address
Valid email addresses
simple@example.com
"user@name"@example.com
very.common@example.com
disposable.style.email.with+symbol@example.com
other.email-with-hyphen@example.com
fully-qualified-domain@example.com
user.name+tag+sorting@example.com (may go to user.name@example.com inbox depending on mail server)
x@example.com (one-letter local-part)
example-indeed@strange-example.com
test/test@test.com (slashes are a printable character, and allowed)
admin@mailserver1 (local domain name with no TLD, although ICANN highly discourages dotless email addresses[10])
example@s.example (see the List of Internet top-level domains)
" "@example.org (space between the quotes)
"john..doe"@example.org (quoted double dot)
mailhost!username@example.org (bangified host route used for uucp mailers)
user%example.com@example.org (% escaped mail route to user@example.com via example.org)
user-@example.org (local part ending with non-alphanumeric character from the list of allowed printable characters)
postmaster@[123.123.123.123] (IP addresses are allowed instead of domains when in square brackets, but strongly discouraged)
postmaster@[IPv6:2001:0db8:85a3:0000:0000:8a2e:0370:7334] (IPv6 uses a different syntax)

Invalid email addresses
Abc.example.com (no @ character)
A@b@c@example.com (only one @ is allowed outside quotation marks)
a"b(c)d,e:f;gi[j\k]l@example.com (none of the special characters in this local-part are allowed outside quotation marks)
just"not"right@example.com (quoted strings must be dot separated or the only element making up the local-part)
this is"not\allowed@example.com (spaces, quotes, and backslashes may only exist when within quoted strings and preceded by a backslash)
this\ still\"not\\allowed@example.com (even if escaped (preceded by a backslash), spaces, quotes, and backslashes must still be contained by quotes)
1234567890123456789012345678901234567890123456789012345678901234+x@example.com (local-part is longer than 64 characters)
i_like_underscore@but_its_not_allowed_in_this_part.example.com (Underscore is not allowed in domain part)
QA[icon]CHOCOLATE[icon]@test.com (icon characters)

Твои правила ломаются больше чем в половине приведённых примеров

Если нужен реальных регэксп для имейла, то вот ответ:
https://stackoverflow.com/questions/201323/how-can...
// derivative of work with the following copyright and license:
// Copyright (c) 2004 Casey West.  All rights reserved.
// This module is free software; you can redistribute it and/or
// modify it under the same terms as Perl itself.

// see http://search.cpan.org/~cwest/Email-Address-1.80/

private static string gibberish = @"
(?-xism:(?:(?-xism:(?-xism:(?-xism:(?-xism:(?-xism:(?-xism:\
s*\((?:\s*(?-xism:(?-xism:(?>[^()\\]+))|(?-xism:\\(?-xism:[^
\x0A\x0D]))|(?-xism:\s*\((?:\s*(?-xism:(?-xism:(?>[^()\\]+))
|(?-xism:\\(?-xism:[^\x0A\x0D]))|)+)*\s*\)\s*))+)*\s*\)\s*)+
|\s+)*[^\x00-\x1F\x7F()<>\[\]:;@\,.<DQ>\s]+(?-xism:(?-xism:\
s*\((?:\s*(?-xism:(?-xism:(?>[^()\\]+))|(?-xism:\\(?-xism:[^
\x0A\x0D]))|(?-xism:\s*\((?:\s*(?-xism:(?-xism:(?>[^()\\]+))
|(?-xism:\\(?-xism:[^\x0A\x0D]))|)+)*\s*\)\s*))+)*\s*\)\s*)+
|\s+)*)|(?-xism:(?-xism:(?-xism:\s*\((?:\s*(?-xism:(?-xism:(
?>[^()\\]+))|(?-xism:\\(?-xism:[^\x0A\x0D]))|(?-xism:\s*\((?
:\s*(?-xism:(?-xism:(?>[^()\\]+))|(?-xism:\\(?-xism:[^\x0A\x
0D]))|)+)*\s*\)\s*))+)*\s*\)\s*)+|\s+)*<DQ>(?-xism:(?-xism:[
^\\<DQ>])|(?-xism:\\(?-xism:[^\x0A\x0D])))+<DQ>(?-xism:(?-xi
sm:\s*\((?:\s*(?-xism:(?-xism:(?>[^()\\]+))|(?-xism:\\(?-xis
m:[^\x0A\x0D]))|(?-xism:\s*\((?:\s*(?-xism:(?-xism:(?>[^()\\
]+))|(?-xism:\\(?-xism:[^\x0A\x0D]))|)+)*\s*\)\s*))+)*\s*\)\
s*)+|\s+)*))+)?(?-xism:(?-xism:(?-xism:\s*\((?:\s*(?-xism:(?
-xism:(?>[^()\\]+))|(?-xism:\\(?-xism:[^\x0A\x0D]))|(?-xism:
\s*\((?:\s*(?-xism:(?-xism:(?>[^()\\]+))|(?-xism:\\(?-xism:[
^\x0A\x0D]))|)+)*\s*\)\s*))+)*\s*\)\s*)+|\s+)*<(?-xism:(?-xi
sm:(?-xism:(?-xism:(?-xism:\s*\((?:\s*(?-xism:(?-xism:(?>[^(
)\\]+))|(?-xism:\\(?-xism:[^\x0A\x0D]))|(?-xism:\s*\((?:\s*(
?-xism:(?-xism:(?>[^()\\]+))|(?-xism:\\(?-xism:[^\x0A\x0D]))
|)+)*\s*\)\s*))+)*\s*\)\s*)+|\s+)*(?-xism:[^\x00-\x1F\x7F()<
>\[\]:;@\,.<DQ>\s]+(?:\.[^\x00-\x1F\x7F()<>\[\]:;@\,.<DQ>\s]
+)*)(?-xism:(?-xism:\s*\((?:\s*(?-xism:(?-xism:(?>[^()\\]+))
|(?-xism:\\(?-xism:[^\x0A\x0D]))|(?-xism:\s*\((?:\s*(?-xism:
(?-xism:(?>[^()\\]+))|(?-xism:\\(?-xism:[^\x0A\x0D]))|)+)*\s
*\)\s*))+)*\s*\)\s*)+|\s+)*)|(?-xism:(?-xism:(?-xism:\s*\((?
:\s*(?-xism:(?-xism:(?>[^()\\]+))|(?-xism:\\(?-xism:[^\x0A\x
0D]))|(?-xism:\s*\((?:\s*(?-xism:(?-xism:(?>[^()\\]+))|(?-xi
sm:\\(?-xism:[^\x0A\x0D]))|)+)*\s*\)\s*))+)*\s*\)\s*)+|\s+)*
<DQ>(?-xism:(?-xism:[^\\<DQ>])|(?-xism:\\(?-xism:[^\x0A\x0D]
)))+<DQ>(?-xism:(?-xism:\s*\((?:\s*(?-xism:(?-xism:(?>[^()\\
]+))|(?-xism:\\(?-xism:[^\x0A\x0D]))|(?-xism:\s*\((?:\s*(?-x
ism:(?-xism:(?>[^()\\]+))|(?-xism:\\(?-xism:[^\x0A\x0D]))|)+
)*\s*\)\s*))+)*\s*\)\s*)+|\s+)*))\@(?-xism:(?-xism:(?-xism:(
?-xism:\s*\((?:\s*(?-xism:(?-xism:(?>[^()\\]+))|(?-xism:\\(?
-xism:[^\x0A\x0D]))|(?-xism:\s*\((?:\s*(?-xism:(?-xism:(?>[^
()\\]+))|(?-xism:\\(?-xism:[^\x0A\x0D]))|)+)*\s*\)\s*))+)*\s
*\)\s*)+|\s+)*(?-xism:[^\x00-\x1F\x7F()<>\[\]:;@\,.<DQ>\s]+(
?:\.[^\x00-\x1F\x7F()<>\[\]:;@\,.<DQ>\s]+)*)(?-xism:(?-xism:
\s*\((?:\s*(?-xism:(?-xism:(?>[^()\\]+))|(?-xism:\\(?-xism:[
^\x0A\x0D]))|(?-xism:\s*\((?:\s*(?-xism:(?-xism:(?>[^()\\]+)
)|(?-xism:\\(?-xism:[^\x0A\x0D]))|)+)*\s*\)\s*))+)*\s*\)\s*)
+|\s+)*)|(?-xism:(?-xism:(?-xism:\s*\((?:\s*(?-xism:(?-xism:
(?>[^()\\]+))|(?-xism:\\(?-xism:[^\x0A\x0D]))|(?-xism:\s*\((
?:\s*(?-xism:(?-xism:(?>[^()\\]+))|(?-xism:\\(?-xism:[^\x0A\
x0D]))|)+)*\s*\)\s*))+)*\s*\)\s*)+|\s+)*\[(?:\s*(?-xism:(?-x
ism:[^\[\]\\])|(?-xism:\\(?-xism:[^\x0A\x0D])))+)*\s*\](?-xi
sm:(?-xism:\s*\((?:\s*(?-xism:(?-xism:(?>[^()\\]+))|(?-xism:
\\(?-xism:[^\x0A\x0D]))|(?-xism:\s*\((?:\s*(?-xism:(?-xism:(
?>[^()\\]+))|(?-xism:\\(?-xism:[^\x0A\x0D]))|)+)*\s*\)\s*))+
)*\s*\)\s*)+|\s+)*)))>(?-xism:(?-xism:\s*\((?:\s*(?-xism:(?-
xism:(?>[^()\\]+))|(?-xism:\\(?-xism:[^\x0A\x0D]))|(?-xism:\
s*\((?:\s*(?-xism:(?-xism:(?>[^()\\]+))|(?-xism:\\(?-xism:[^
\x0A\x0D]))|)+)*\s*\)\s*))+)*\s*\)\s*)+|\s+)*))|(?-xism:(?-x
ism:(?-xism:(?-xism:(?-xism:\s*\((?:\s*(?-xism:(?-xism:(?>[^
()\\]+))|(?-xism:\\(?-xism:[^\x0A\x0D]))|(?-xism:\s*\((?:\s*
(?-xism:(?-xism:(?>[^()\\]+))|(?-xism:\\(?-xism:[^\x0A\x0D])
)|)+)*\s*\)\s*))+)*\s*\)\s*)+|\s+)*(?-xism:[^\x00-\x1F\x7F()
<>\[\]:;@\,.<DQ>\s]+(?:\.[^\x00-\x1F\x7F()<>\[\]:;@\,.<DQ>\s
]+)*)(?-xism:(?-xism:\s*\((?:\s*(?-xism:(?-xism:(?>[^()\\]+)
)|(?-xism:\\(?-xism:[^\x0A\x0D]))|(?-xism:\s*\((?:\s*(?-xism
:(?-xism:(?>[^()\\]+))|(?-xism:\\(?-xism:[^\x0A\x0D]))|)+)*\
s*\)\s*))+)*\s*\)\s*)+|\s+)*)|(?-xism:(?-xism:(?-xism:\s*\((
?:\s*(?-xism:(?-xism:(?>[^()\\]+))|(?-xism:\\(?-xism:[^\x0A\
x0D]))|(?-xism:\s*\((?:\s*(?-xism:(?-xism:(?>[^()\\]+))|(?-x
ism:\\(?-xism:[^\x0A\x0D]))|)+)*\s*\)\s*))+)*\s*\)\s*)+|\s+)
*<DQ>(?-xism:(?-xism:[^\\<DQ>])|(?-xism:\\(?-xism:[^\x0A\x0D
])))+<DQ>(?-xism:(?-xism:\s*\((?:\s*(?-xism:(?-xism:(?>[^()\
\]+))|(?-xism:\\(?-xism:[^\x0A\x0D]))|(?-xism:\s*\((?:\s*(?-
xism:(?-xism:(?>[^()\\]+))|(?-xism:\\(?-xism:[^\x0A\x0D]))|)
+)*\s*\)\s*))+)*\s*\)\s*)+|\s+)*))\@(?-xism:(?-xism:(?-xism:
(?-xism:\s*\((?:\s*(?-xism:(?-xism:(?>[^()\\]+))|(?-xism:\\(
?-xism:[^\x0A\x0D]))|(?-xism:\s*\((?:\s*(?-xism:(?-xism:(?>[
^()\\]+))|(?-xism:\\(?-xism:[^\x0A\x0D]))|)+)*\s*\)\s*))+)*\
s*\)\s*)+|\s+)*(?-xism:[^\x00-\x1F\x7F()<>\[\]:;@\,.<DQ>\s]+
(?:\.[^\x00-\x1F\x7F()<>\[\]:;@\,.<DQ>\s]+)*)(?-xism:(?-xism
:\s*\((?:\s*(?-xism:(?-xism:(?>[^()\\]+))|(?-xism:\\(?-xism:
[^\x0A\x0D]))|(?-xism:\s*\((?:\s*(?-xism:(?-xism:(?>[^()\\]+
))|(?-xism:\\(?-xism:[^\x0A\x0D]))|)+)*\s*\)\s*))+)*\s*\)\s*
)+|\s+)*)|(?-xism:(?-xism:(?-xism:\s*\((?:\s*(?-xism:(?-xism
:(?>[^()\\]+))|(?-xism:\\(?-xism:[^\x0A\x0D]))|(?-xism:\s*\(
(?:\s*(?-xism:(?-xism:(?>[^()\\]+))|(?-xism:\\(?-xism:[^\x0A
\x0D]))|)+)*\s*\)\s*))+)*\s*\)\s*)+|\s+)*\[(?:\s*(?-xism:(?-
xism:[^\[\]\\])|(?-xism:\\(?-xism:[^\x0A\x0D])))+)*\s*\](?-x
ism:(?-xism:\s*\((?:\s*(?-xism:(?-xism:(?>[^()\\]+))|(?-xism
:\\(?-xism:[^\x0A\x0D]))|(?-xism:\s*\((?:\s*(?-xism:(?-xism:
(?>[^()\\]+))|(?-xism:\\(?-xism:[^\x0A\x0D]))|)+)*\s*\)\s*))
+)*\s*\)\s*)+|\s+)*))))(?-xism:\s*\((?:\s*(?-xism:(?-xism:(?
>[^()\\]+))|(?-xism:\\(?-xism:[^\x0A\x0D]))|(?-xism:\s*\((?:
\s*(?-xism:(?-xism:(?>[^()\\]+))|(?-xism:\\(?-xism:[^\x0A\x0
D]))|)+)*\s*\)\s*))+)*\s*\)\s*)*)"
  .Replace("<DQ>", "\"")
  .Replace("\t", "")
  .Replace(" ", "")
  .Replace("\r", "")
  .Replace("\n", "");

private static Regex mailbox =
  new Regex(gibberish, RegexOptions.ExplicitCapture);

Худший ответ: А это действительно так необходимо?
https://emailregex.com/