ながら / いながら / ながらも

1. 1While doing A, the same subject does B, the main action.Ex. 1
2. 2Although A is the case, B holds, a contrast between two facts.Ex. 2

The simultaneous sense is everyday and neutral. The ながら clause gives the background or secondary action, and the main action comes at the end. The concessive sense, especially ながらも, sounds somewhat more formal or written. It commonly follows adjectives, nouns and stative expressions like いながら. It states a contrast calmly, without the blame of くせに or the frustration of のに.

• つつN2「つつ」 also has both the “while doing…” and concessive meanings, but it attaches only to the verb continuative (masu-stem) form and is written language. With verbs it can be swapped with 「ながら」 in a more formal tone and is rare in speech, and its concessive use usually pairs with verbs like 「知る」 and 「思う」.
• 〜つつもN3「つつも」 has only the concessive meaning; it attaches only to the masu-stem of verbs — mostly psychological verbs such as 「知る」 and 「思う」 — and is more at home in writing than 「ながらも」. The two are interchangeable for concessive use with verbs, but with nouns and adjectives only 「ながら(も)」 is possible.
• くせにN3「くせに」 is close only to the concessive meaning, but it carries strong blame and contempt, leans colloquial, and can end a sentence with the second clause left unstated. It attaches to the plain form — 「の」 after nouns, 「な」 after na-adjectives — and neutral statements cannot be replaced with 「くせに」.
• のにN4「のに」 has no “while doing…” meaning and is close only to the concessive sense of 「ながら(も)」. 「のに」 often adds surprise, dissatisfaction, or regret and can be used at the end of a sentence, while 「ながら(も)」 is more objective and 「ながらも」 is more at home in writing.
• もののN2「ものの」 expresses only concession and is close to the concessive 「ながら(も)」, with the two sometimes interchangeable. 「ものの」 is more at home in writing, usually attaches to the ta-form, and its second clause often falls short of expectations with a sense of regret; with nouns, you must use 「である＋ものの」.
• と同時にN2「と同時に」 stresses that two things happen at the very same instant, allows the two clauses to have different subjects, and attaches to the dictionary form, the ta-form, or a noun. It can also present two parallel sides of something (“both … and …”), unlike 「ながら(も)」, which signals a contrast.

つつ and 〜つつも are more formal, written counterparts of the simultaneous ながら and concessive ながらも. ものの is a written 'although' and と同時に marks events at the same moment, while くせに adds criticism and のに adds surprise or dissatisfaction that neutral ながらも lacks.