So minus some decent sounding monitors, I'm all set t record some covers! Problem is, I can't get the timing of certain tracks right in post production.

For example, a song like "Seek and Destroy" by Metallica is easy, because all you have to do is listen for the first guitar and then you play right at the same time and BAM! you've got the timing!

But a song like this one, with drums in the beginning.... Idk how you find the timing between the backing track, and when to start playing... I'm really confused because i play along to the original track with my ipod, but maybe there's an easier way?

I just wanna get the timing right and that's what's consistently fucking me up and preventing me from actually getting my youtube channel off of the ground! Someone please help. Thank you.

If it helps you to know, I'm not mic'ing an amp... I'm recording directly int the DAW with either an amp sim pedal (JOYO) or using plug-ins.
I'm a bit confused to what the problem is, but if you don't know when to start playing;

1. Listen to the song 1000 times and learn all timing changes by ear
2. Google for the BPM of the song in particular and sync up the backing track with the DAW grid after having set the BPM. Use the DAW metronome to help you.

About getting your YT channel off the ground if you're doing covers...well I'm not Mr. Popular myself but after watching your video, I recommend you to work on your guitar tone (it's too harsh and distorted IMO, try overdrive instead of distortion), sound (learn to mix the actual guitar recording with the backing track and not just post the camera sound) and camera work (most popular and not so popular cover channels have some fancy cameras and do different angles, good lightning, just eye candy that doesn't really say anything about your playing but get you more views somehow).

I hope that helped and good luck!