The most frustrating: Sideboard

Please tell me I'm not the only one that finds sideboarding the most frustrating and the most time-consuming in deck building.

Is it just me that my initial options for sideboarding will always exceed the restricted 15 cards?

Also, is it just me or that more time is actually spent on sideboarding strategies rather than actually making sure the deck works?

Personally I love to play home-brew decks, but I'm not really an avid fan of brewing tons of decks and throw them around. To me, I prefer to build 1 or 2 competitive or non-casual decks, build them up proper with the proper tuning and just play with it. I really don't see the need to have 10 Modern decks or EDH decks when I only have time and energy to just play 1 at a time. Also, having lesser decks means being able to spend more time practicing and focus on being good at solely just one deck, I'm able to tune and make changes faster and more efficiently.

Hmm.. to side or not to...

But, here comes the part which frustrates myself; I prefer home-brew decks over competitive net-decks. Sure, I may take ideas from primers and net decks, but in the end, the final product is ensured to have some sort of personal expression or originality in it.  I actually dismantled a UW midrange deck after playing for a single event for my own homebrew. I personally preferred the latter deck still, but I digress.

If you look at my (almost) weekly gameplay reviews, I have been reviewing my gameplay for my Ally reanimator deck for months and I have not even fixed a finalized sideboard. The deck was a homebrew, which  which I have been working for almost a YEAR!

The "worst" part of the deck building that I have found when home-brewing a deck is the sideboard.
The sideboard is restricted to just 15 cards; we can never find enough space for our ideal list. Please tell me I'm not the only one who thinks 15 cards is, although the right number, really much crammed in space to jam in all our wants. I always have the problem in which I have a list of 20+ cards as ideas for sideboarding. After cutting out 50% of them, I then included the multiples, which always ended up more than the 15 slots, which then I went ahead to remove the cards that are too narrow in its hate or the intended disruption. Finally, I'll end up with 16 cards, not knowing which to cut (In fact, at this point of writing, my Ally Reanimator deck actually has 16 cards in the sideboard, which I left out the third Stony Silence out in favor of the third Pithing Needle.)

The need to separate the wants and needs is really crucial. But, in most games, our needs and wants are really separated by a vague line to be honest. That's frustrating...

Another issue that I can think of as to why sideboard is the "worst" part of the entire deck building journey is the almost lack of originality. Okay, I'm sure I'm going to get a lot of heat from this, but hear me out! When it comes to the sideboard, more time is spent actually on analyzing local meta and this can be frustrating as the local meta differs, but the decks that are present is usually not. The main difference is the percentage variation of the different archetypes and decks present that makes up to the meta.

Building on the point mentioned above, since so much time is spent on analyzing meta, it naturally meant that more time is spent building the sideboard (which is a good thing by the way; means I am really looking into the meta and fighting against it properly). But, it still doesn't give much variation to the sideboard in terms of originality. Strong sideboard cards have already been tested and proven to be effective against certain decks and match-ups. So, even if its a home-brew deck, the sideboard may eventually be winding up as the same as the other guy across the room, playing the same archetype.

Sure, I'm not blind to notice that there are variations to the "hate" and stax cards that are used against match-ups; I'm pointing out that the sideboards in the certain archetype would eventually look the same. For example, creature-heavy decks would eventually use Kataki, War's Wage over Stony Silence against Affinity match-ups. The variation is there in the cards, but not the hate. Eventually, the sideboard is not just dependant on the deck I make, but also what decks other people make.

In essence, the most frustrating thing in Sideboard building is not actually the building; that's the easy part: finding the cards to hate. But, it is not so simple as to just jam in 15 hate cards and done.

How does the hate cards hinder your game-plan? 
How does the additional cards going to affect the mana curve? 
How does the cards going to affect your other games? 
Are there better options out there? 
Are the options flexible enough to cover more than intended? 
What cards are you going to side out? 

So many questions to think through and answer before I can actually decide on a good sideboard. It's the analysis and research needed as downtime to understand the local meta in your community and actually plan and work against it. It is also the time needed to look at your decklist and understand the minor synergy between the cards, how they interact each other. By including the new cards from the sideboard, how are the interactions going to be different? How the game-plan is going to change? That's the frustration.

It is very clear to anyone who played a decent amount of time in MTG to know that the sideboard is the most important 15 cards out of the 75.  It is the crucial plan in your entire deck that determines your decks' viability against the meta, literally making and breaking your games.

The meta is forever changing as more deck ideas will come up overtime. We only have to keep up.