Does Allah actually love someone who keeps messing up and coming back, or does He just tolerate us out of obligation?

The picture you are carrying is of a weary master who puts up with you and sighs each time you come back. That picture is not Allah. It is the tiredness of our own hearts painted onto the sky. What He has told us about Himself is something else entirely.

He does not describe grudging patience toward the one who returns. He describes love, chosen and stated plainly:

“Indeed, Allah loves those who turn to Him in repentance.”

Qur’an, Al-Baqarah 2:222 · meaning

Notice that He does not say He loves those who never fall. He names the returners themselves. Coming back, again and again, is not something He merely puts up with; it is the very thing He loves. Your returning is not a nuisance to Him.

And in case we still imagine the welcome as cool and formal, the Prophet, peace be upon him, gave us an image. A traveller in the desert loses his camel, and with it his water and his provision, so he lies down to die. Then the camel is standing in front of him.

“Allah is more joyful at the repentance of His servant than one of you who loses his camel in a desolate land and then finds it again.”

The Prophet (peace be upon him), Sahih al-Bukhari and Sahih Muslim (Bukhari 6309 / Muslim 2747a) · meaning

That shout a rescued man cannot hold back is closer to how your Lord receives you than any sense of duty. Much of what we become is shaped by whether we believed someone was glad of us, and here is the One who made you, glad at your return. So come back as often as you slip. Each homecoming is met with joy, not a frown.

One small step: Tonight, before sleep, say once, “Ya Allah, here I am, turning back to You,” and let yourself believe He is glad to hear it.