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In Shmot 40:35, the text reads (via the Chabad site):

Moses could not enter the Tent of Meeting because the cloud rested upon it and the glory of the Lord filled the Mishkan.
לה.וְלֹא יָכֹל משֶׁה לָבוֹא אֶל אֹהֶל מוֹעֵד כִּי שָׁכַן עָלָיו הֶעָנָן וּכְבוֹד יְהֹוָה מָלֵא אֶת הַמִּשְׁכָּן

Rashi recognizes that this contradicts another pasuk and writes:

Moses could not enter the Tent of Meeting: But one [other] passage says: “And when Moses would enter the Tent of Meeting” (Num. 7:89), [which is an apparent contradiction]. The third passage [verse 35] came and reconciled them: “because the cloud rested upon it.” You may henceforth say that as long as the cloud was upon it, he could not enter, [but when] the cloud withdrew, he would enter and [God] would speak with him. -[from Torath Kohanim, Shalosh Esrei Middoth, Thirteen methods, Section 8]

But the next pasuk reads

36.When the cloud rose up from over the Mishkan, the children of Israel set out in all their journeys.

So when there was no cloud, Moshe could NOT have gone in to the tent because that was when the people traveled.

How exactly is Rashi reconciling the two statements (Moshe could not go in, and Moshe did go in) if what he cites flies in the face of another pasuk?

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Rashbam on that verse brings the same idea as Rashi, but explains further. The event that allows Moshe to enter the tent was the cloud being "reduced" (מצומצם) such that it only was over the ark (and not the entire tent). In his words (and my translation):

ולא יכול משה לבא אל אהל מועד – בשעת הקמתו, כי שכן עליו הענן – מיד, להראות חיבתו של הקב״ה על ישראל. אחרי כן היה מסתלק הענן מתוך האהל ושכן על הארון, כדכת' ונועדתי לך שם ודברתי אתך {וגו'} מבין שני הכרובים (שמות כ"ה:כ"ב), ואז בא משה אל אהל מועד, כדכת' ובבא משה אל אהל מועד לדבר אתו וישמע את הקול וגו' מבין שני הכרובים וידבר אליו (במדבר ז:פ"ט). וכן את מוצא בבית עולמים: ולא יכלו הכהנים לעמוד לשרת מפני הענן כי מלא כבוד י"י את בית י"י (מלכים א ח':י"א), בשעת השלמת הבית היה הקב״ה מקדשו בענן, ואחר כך היה מצמצם שכינתו על הארון בין הבדים. ואשר שם לבו לדבר יוצרינו אל יזוז מנימוקי זקני רבינו שלמה ואל ימוש מהם, כי רוב הלכות ודרשות שבהם קרובים לפשוטי המקראות [ומיתורם או משינוי] הלשון יש ללמוד כולם, וטוב אשר תאחוז בזה אשר פירשתי וגם מזה אל תנח ידך.

And Moses was unable to enter the Tent of Meeting – while it was being erected, for the cloud rested upon it – immediately, to show God's love for Israel. After that the cloud removed itself from the Tent and rested upon the ark, as it's written (Ex. 25:22): "And I will meet with you and speak with you... between the cherubs", and then Moses entered the Tent of Meeting, as it's written (Num 7:89): "And when Moses would enter the Tent of Meeting to speak with Him, he would hear the Voice... from between the two cherubs and it would speak to him". You will find similarly regarding the Eternal Temple (1 Kings 8:11): "And the priests were not able to stand and minister because of the Cloud, for the Glory of God filled the House of God", as the Temple was finished, God sanctified it with the cloud, and later he reduced his Presence to above the ark between the poles.

He who pays attention to the matters of our Creator should not depart from the explanations of my grandfather Rabbi Shlomo (Rashi), for most of his halachot and drashot are close to the plain meaning of the written text, and from its additions [ie. extra letters/words] or changes of language we can learn them all, and it would be good to accept what I explained and do not ignore it.

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