I know you have been here in this technology for a quite long time which I consider that you have knowledge in this technology as we know that investing in this technology is high risk. Since you have done your research I pretty sure that at this time you will guarantee to become rich by next year but put in your mind that everything you read thru google is just speculation. It's not a guarantee that the price for 2019 will become bullish.  

If you have 50 thousand dollars to gamble away in a bitcoin bet, why not divide it more ? I mean instead of 10 thousand dollars for each entry, how about you do something like 5% each entry for 20 times. That way you can either use it weekly or even monthly and you can put money in it for a long period of time. That would mean you will take less risks for a potential decrease in the price but you are giving up potential price uptick as well.

If you really believe bitcoin will go up soon than you can put your money weekly for 20 weeks and that way you will be all invested this summer. Or, if you think it will take longer you can invest monthly and you will be all invested in 2020 at the earliest. I think putting it all in 5 times is not a smart move, I would suggest at least 10 and better yet 20 for that.

Looks good. Honestly, prices are pretty low right now and the general consensus is that we're close to the floor.

Your strategy seems a lot like dollar cost averaging, whereby you buy a predetermined amount of BTC each period regardless of what the price is. In my opinion, this is quite a good strategy for accumulating coins for the long run especially in a bear market, as you are essentially accepting that it is pretty much impossible to predict what the lowest of lows are going to be, but rather, focus on averaging out the entry points of your long positions so that they are most profitable in the long run.

As for the coins that you purchased for $6k+, I would not worry about it. Again, by buying now, you are able to lower your average entry point. And if you believe in bitcoin in the long run, whether in terms of institutional investors, or adoption over time, as I do, then breaking $6k again is only a matter of time given the potential demand in the future.

Wow, your story seems oddly similar to mine - bought a bunch of BTC late 2013/2014/early 2015, sold it all at the bottom in 2015 for a couple thousand, though then i bought a bunch of bitcoin and some ethereum last year, didn't sell any at the top and managed to lose a bunch trading during the crash haha. Though I just started buying more the past few weeks once it went under $4k. And coincidentally I also plan on buying $50k worth of Bitcoin (picked up $7k so far), though I'll do it over the next few months.

Honestly buying Bitcoin right now or in the next few months is the absolute best investment you could make now. I have zero reservations about throwing $50k into Bitcoin over the next few months (and $50k is an absurd amount of money for me, outside of my crypto portfolio at the end of last year and the first half of this year I've never had $50k in my life before - I'll only have it now cuz the company I work for is about to sell so I'll make some decent money). Still, zero reservations. I'm hoping to pick up more than 12 or 13 more Bitcoin with that money and plan to sell it at $70k which I figure will EASILY happen on the next boom in a few years.

Of course if you would stress about putting that much money in you could always only put say half of it in now and wait till maybe mid next year or whenever a solid new bull market has begun to put the other half in, you'd just get a lot less for your money then, but if you view Bitcoin as risky (I don't) then that would put your mind at ease and you'd still make a ton of money if you wait until the price is booming again in say the high 5 digits.

If you're having doubts, then don't do it all at once. Studying is not a few hours commitment; if you want to really digest what's happening in the market, I think few hours isn't enough to get all the knowledge you needed before investing. $50k is a lot of money in my books, and I could easily create a business that will run for years had I chosen to not invest it on crypto. There are always risks on every form of investment available to Man, and you need to decide whole-heartedly if that risks are worth to take for the potential reward.

Seeing bitcoin as 'too big to fail' is also wrong, and you really need to evaluate your plan since you might get it wrong and you might kick yourself once bad things happen. I'm not a crypto hater nor a non-believer, I'm just stating that anything can happen for bitcoin and crypto investments in general.