How to say he was accustomed to flying alone, and he had flown this route in his imagination many times. in Japanese

1)彼(kare) (ok) that , or something understood without naming it directly)/that person/over there/hey/eh?/thatは(ha) (int) indicating a subject/yes/indeed/well/ha!/what?/huh?/sigh1(1) (num,pref) one/best in/the most in人(nin) (suf) -ian/-er/man/person/peopleで(de) (prt) indicates location of action/at/in/indicates time of action/indicates means of action/cause of effect/by/and then/so/indicates continuing action/ indicates certainty, emphasis, etc.飛ぶ飛ぶ(tobu) (v5b,vi) to jump/to leap/to spring/to bound/to hop/to fly/to soarことにことに(kotoni) (adv) especially/particularly/unusually/above all/additionally慣れ慣れ(nare) (n,vs) practice/practise/experienceていたno dictionary result, likely a conjigated verbno dictionary result, likely a conjigated verb。(。) Japanese period "."そしてそして(soshite) (conj) and/and then/thus/and now彼(kare) (ok) that , or something understood without naming it directly)/that person/over there/hey/eh?/thatは(ha) (int) indicating a subject/yes/indeed/well/ha!/what?/huh?/sigh想像想像(souzou) (n,vs,adj-no) imagination/guessの(no) (prt) indicates possessive/nominalizes verbs and adjectives/substitutes for "ga" in subordinate phrases/indicates a confident conclusion/ indicates emotional emphasis/indicates question中(naka) (n,adj-no) inside/within/while/among/amongst/between/we/our/my spouse/ imperial palace grounds/emperor/ i/meで(de) (prt) indicates location of action/at/in/indicates time of action/indicates means of action/cause of effect/by/and then/so/indicates continuing action/ indicates certainty, emphasis, etc.何度何度(nando) (n) how many times?/how often?もこもこ(moko) (adj-t,adv-to) dim/vague/indistinct/faint/obscureの(no) (prt) indicates possessive/nominalizes verbs and adjectives/substitutes for "ga" in subordinate phrases/indicates a confident conclusion/ indicates emotional emphasis/indicates question経路経路(keiro) (n) course/route/path/channel/process/meansを(wo) (prt) indicates direct object of action/indicates subject of causative expression/indicates an area traversed/indicates time over which action takes place/indicates point of departure or separation of action/indicates object of desire, like, hate,飛んno dictionary result, likely a conjigated verbno dictionary result, likely a conjigated verbで(de) (prt) indicates location of action/at/in/indicates time of action/indicates means of action/cause of effect/by/and then/so/indicates continuing action/ indicates certainty, emphasis, etc.い(i) (prt) strengthens a question, assertion, etc.たのだno dictionary result, likely a conjigated verbno dictionary result, likely a conjigated verb。(。) Japanese period "."    
kareha 1 nin de tobu kotoni nare teita 。 soshite kareha souzou no naka de nando mokono keiro wo ton deitanoda 。
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2)彼(kare) (ok) that , or something understood without naming it directly)/that person/over there/hey/eh?/thatは(ha) (int) indicating a subject/yes/indeed/well/ha!/what?/huh?/sigh1(1) (num,pref) one/best in/the most in人(nin) (suf) -ian/-er/man/person/peopleで(de) (prt) indicates location of action/at/in/indicates time of action/indicates means of action/cause of effect/by/and then/so/indicates continuing action/ indicates certainty, emphasis, etc.飛ぶ飛ぶ(tobu) (v5b,vi) to jump/to leap/to spring/to bound/to hop/to fly/to soarことにことに(kotoni) (adv) especially/particularly/unusually/above all/additionally慣れ慣れ(nare) (n,vs) practice/practise/experienceていたそしてno dictionary result, likely a conjigated verbno dictionary result, likely a conjigated verb彼(kare) (ok) that , or something understood without naming it directly)/that person/over there/hey/eh?/thatは(ha) (int) indicating a subject/yes/indeed/well/ha!/what?/huh?/sigh想像想像(souzou) (n,vs,adj-no) imagination/guessの(no) (prt) indicates possessive/nominalizes verbs and adjectives/substitutes for "ga" in subordinate phrases/indicates a confident conclusion/ indicates emotional emphasis/indicates question中(naka) (n,adj-no) inside/within/while/among/amongst/between/we/our/my spouse/ imperial palace grounds/emperor/ i/meで(de) (prt) indicates location of action/at/in/indicates time of action/indicates means of action/cause of effect/by/and then/so/indicates continuing action/ indicates certainty, emphasis, etc.何度何度(nando) (n) how many times?/how often?もこもこ(moko) (adj-t,adv-to) dim/vague/indistinct/faint/obscureの(no) (prt) indicates possessive/nominalizes verbs and adjectives/substitutes for "ga" in subordinate phrases/indicates a confident conclusion/ indicates emotional emphasis/indicates question経路経路(keiro) (n) course/route/path/channel/process/meansを(wo) (prt) indicates direct object of action/indicates subject of causative expression/indicates an area traversed/indicates time over which action takes place/indicates point of departure or separation of action/indicates object of desire, like, hate,飛んno dictionary result, likely a conjigated verbno dictionary result, likely a conjigated verbで(de) (prt) indicates location of action/at/in/indicates time of action/indicates means of action/cause of effect/by/and then/so/indicates continuing action/ indicates certainty, emphasis, etc.い(i) (prt) strengthens a question, assertion, etc.たのだno dictionary result, likely a conjigated verbno dictionary result, likely a conjigated verb    
kareha 1 nin de tobu kotoni nare teitasoshite kareha souzou no naka de nando mokono keiro wo ton deitanoda
Grammer form日常会話 (Casual form)Casual form (nichijoukaiwa)
everyday casual language, commonly used between friends and family.
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