Hayo,

I have a few questions, cause this system is quite complicated and I'm confused. Especially as a new player, I don't want to click aimlessly.

Im on season character, Guardian. Enhanced my gear to PRI and Im level 49 atm.

I also made a second character Maegu but left her at level 24 ( kinda enjoy her playstyle more ). Now the question is, should I push Guardian to level 60 and finish the Season Reward tree and then use Fughar Timepiece? Or use Fughar Timepiece now to transfer ( whatever it transfers ) to Maegu? Will my Guardian still benefit from Season boosts? Or everything transfers to Maegu? Even Season Reward Tree?

Also seen a few videos where people do that, but after the transfer, they get the character NARU gear from that deer NPC. So not only do they keep enhanced gear on transferred characters but the previous one has NARU gear ( as they claim is not left naked ).

In the end, I would like to enjoy playing both characters. To spice up the monotony a bit.

My thankies.

Best is to get to level 60+ on your Guardian before using the timepiece - you say at the end of your post you want to enjoy playing both?  But if you're not enjoying playing the Guardian, you could just timepiece to the Maegu now.  You can only have one season character at a time.

A level 49 or under character can be useful for things like lifeskilling where you don't want to be subject to PvP, so that wouldn't be a loss, necessarily. 

Once you use the timepiece, all season benefits go to the that character (including the "reward tree").  The previous season character becomes a normal character.  In your case, this means that you would then finish all the season activities on the Maegu, including enhancing the gear, which can only be used for a season character (until graduation).

As for the Guradian, after using the timepiece you can use Naru or any other gear except for season Tuvala.

In addition to what Entropoid said, I want to point out that that Naru gear at PEN can be traded for a set of Narchillan gear via Fughar. It's a once per family quest, but you can rebox the weapons and pass them on to a different class later if you like. 

Narchillan is a better set than Naru.

So if you want to get two characters to level 60+, you can continue in the season with your guardian and then timepiece.  Or you can timepiece and continue with the Maegu and then level the guardian at a later date. But if you want to play both eventually, I'd stay on the guardian for now.

Especially considering you are only level 49 and haven't tried out the Awakening and Succession specs yet.

The best option would be to continue as is for the moment on your guardian. Once you're like lvl 61 and got PEN/TET tuvala gear you could timepiece it to another character you'd like. 
Keep note of the following things: 

- you can only have one season character at a time. WHen you timepiece to a new character your previous one (in your case your guardian) would be set as a normal character.

- Seasonal rewards can only be claimed once per seasonal characters so if you timepiece to another character you won't be able to claim previous rewards that you've already claimed again. 

- Seasonal gear has to be converted to your new character that you've transferred to. 

- Both your new and old character will have the same EXP as your old character. so if your guardian is level 60 and 34% then your new character will also gain that level. (hence why i advise you to keep playing your guardian longer so you wont have to double level them.)