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Please consider the following conditional statement:

If I would eat my lunch, I would remain healthy.

Some people say that the "would" after "If I" should be omitted for the following reasons:

1.) "If I would" raises two hypotheticals and thus harder to comprehend.

2.) For stylistic reasons, two "would" in one sentence don't read well.

But does replacing "will/would" with "am/was going to" address the first concern? Will it read as well as "If I eat my lunch, I would remain healthy."?

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You seem to be confused on how "would" is used and what it even means. "Would" creates a conditional phrase, not a hypothetical. Hypotheticals are created using the subjunctive mood and often use the conditional in the second clause:

"If I were to eat my lunch, I would remain healthy."

In this sentence, you can't put "would" where "were" is and have it be right. "Were" expresses the past subjunctive mood of "to be." The conditional "would" only happens in the next clause after the comma.

There is nothing that prevents having "would" twice in a single sentence:

If my friend sat here, I would give him a big hug then would feed him my lunch.

Your last sentence is also not grammatically correct. It should say:

If I ate my lunch, I would remain healthy.

This sentence also uses the past subjunctive mood. For verbs other than "to be," the past subjunctive mood happens to use all of the same words as the past indicative tense, so sometimes people mistake them. Make no mistake, though; in the above sentence, you "ate" is not the preterit, it is the subjunctive. Moreover, you can't properly insert "would" into the "if" clause of that sentence as you did.

Finally, you give the following example:

If I was going to...

"Was" is incorrect. Because the past subjunctive mood uses the same words as the preterit tense in all verbs except "to be," people often think that the past subjunctive of "to be" is the same as the preterit, but it's not. Where the preterit is "was," the past subjunctive is "were." The proper way to say the above hypothetical would be:

If I were going to...

Here is a link that explains using "was" instead of "were" when making a hypothetical conditional statement (a.k.a. second conditional) is incorrect:

http://grammar.ccc.commnet.edu/grammar/conditional2.htm

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  • @user15883 : As I explained above, no, it would not be grammatically correct. The "if" clause requires "were," not "would." "Would" is only used in the phrase after the "if" clause, which is often called the "then" clause.
    – Benjamin Harman
    Commented Jan 10, 2016 at 5:19
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    If I was going to be a woman, I would want to be as beautiful as possible. (Dustin Hoffman). People use "was going to" in conditional sentences all the time, it may be seen as informal, or casual speech.
    – Mari-Lou A
    Commented Jan 10, 2016 at 7:59
  • Mari-Lou A : People say "could care less" all the time. People also say, " 'Who' do you want to go with?" Just because many people say something improperly doesn't make it proper. As for movie lines, of course they employ improper grammar. Dramatic characters are intentionally flawed. If everyone spoke in perfect grammar on screen or in a book, it wouldn't be very believable or compelling. Look at Jack Kerouac and J.D. Salinger. Their characters used horrendous grammar. What about Mark Twain? Fiction doesn't set the bar for proper grammar.
    – Benjamin Harman
    Commented Jan 10, 2016 at 8:13
  • But native people talk like that, and if enough English speaking people adopt the meaning, usage of a phrase, and a particular structure then it becomes standard. Do you never split your infinitives? Do you never end a sentence with a preposition? Do you always use "whom" correctly? "Who do you love" is accepted as being "standard" nowadays, but what about thirty or fifty years ago?
    – Mari-Lou A
    Commented Jan 10, 2016 at 10:02

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