In Need of Advice: Large Amounts / Withdrawing Options

Good afternoon!

I am new to this site, and it seems there are lots of people here that have knowledge in this area.  I would like to provide some background and I am seeking advice from those of you who are experienced, and/or could point me in the right direction. 

I currently use one of the reputable offshore books.  I have a large amount of money in the book at the moment.  (50,000 +).  I would like to consider withdrawing some of this money.  I am in no rush to withdraw - meaning, I don't need the money to become liquid, quickly.  What my overarching concern is are the record keeping issues.  Let me elaborate.

I understand that Bitcoin is by far the most quick, easy, and convenient to get my money withdrawn.  However, this poses some transactional risks.  I currently have a wallet with Blockchain, which I would use as the first step in receiving a Bitcoin distribution from the Book.  Then, I can move from the Blockchain Wallet, to my CoinBase wallet - when I desire to sell the bitcoin to convert to dollars.  This method, however, poses risks such as:

1.  CoinBase will report any amount over $20,000 of Bitcoin sold during a calendar year to the IRS through Form 1099.  It appears, then, I could utilize Coinbase to sell less than $20,000 each year, but then I am capped and cannot use Bitcoin anymore.  That's my first issue I'm seeking advice on.  Namely - are there other cryptocurrency sites that are not as highly visible or regulated that will report significant transaction amounts to the IRS?  If so, what are they or where do you recommend I go?  

Would it be a viable option to have exchange accounts on multiple exchanges like CoinBase, Kraken, BitStamp and withdraw 10-15K on each once per year?

Alternatively, the Book appears to allow other Crypto Methods, so perhaps there is another crypto currency, that is not as visible, and an exchange that let's me sell it and convert to dollars right to my bank account - similar to Coinbase?  I don't know, and I'm seeking advice on this issue.

2.  It appears the Book will allow me to withdraw a check, $3,000 Max at a time.  I have never done a check withdrawal before.  I don't know how these work when it comes to depositing them in a bank.  For instance, when I get these checks, do they have any special issues with depositing?  Can I mobile deposit these checks?  What issues, if any, would I run into?  Practically speaking, this appears like a reasonable option, but means I have to request 3K checks for the next 20 weeks for instance.  Is that feasible?  Does this avenue give me problems?

3.  Bank Wire:  I am assuming that if I get a Bank wire directly to my bank account - I will have an issue?  Perhaps my Bank will flag it?  Hold it up?  I do not know, I have never had experience with this route?  Then, does this pose any tax issues?

These are my three options - and I'm seeking guidance from experienced individual's on how to navigate the situation to best achieve the goals of :  Gaining access to the money in my account / doing so safely with minimal records or documentation.  

One Last Item:  How much money would you feel comfortable "keeping" on the Book's site?  I mentioned I have excess of 50,000 there now, and I didn't know if this is just an average figure for an offshore - and where that type of amount would be in comparison to the a Book's average player balance?  Is 50,000 USD high?  Is 150,000 USD high?   Thoughts on this would be greatly appreciated.

Thank you for your time, and I look forward to hearing your responses and thoughts.  Again, I'm a novice when it comes to withdrawing - so any valuable information is much appreciated.  

Hello -  

Wanted to make a quick update.  

I did attempt a check.  It was a nice option.  

Will this pose any issues for me, if I just got a check once a month?

yo mezzi, in the future, maybe consider several different accounts with different books so you can withdrawl i few thousand from them at 1 time instead of 1 big attention attracting check. maybe the book you dealt with is a vacation resort so you can go there to pick up cash if they offer that transaction, doubtful though. really dont have insight with crypto currencies, id like to help but.... and 1 other thing, with much respect to you, are you fucking crazy to keep that kind of money in an offshore account ???? just read thru these threads about the nightmares about players getting their accounts shut off and money confiscated. you would be a prime target to have you account shut down if you went on a massive hot streak. theyd call you a professional and remind you that they dont not honor wagers from professionals, therefore you wagers are void. play small ball with several books and stay under the radar.

Thank you for the advice.  

Honestly, I do / did not know how much one should keep in an offshore account to be fair?  

Bitcoin withdrawals become a pain because the amount of money in the bitcoin machine. I usually find a couple hundred I a lot of them so that could pose a problem all though bitcoin is super easy. It’s sounds like Heritage but maybe not. Take a 3k check every week (12k monthly). In 4 months you will have your 50k (48k to be exact).

Thank you for this response.  So, could I ask a follow up question?

Do you think that taking 3K a week in a foreign bank account check, is eventually going to arouse suspicion from a banking institution?   Especially when the account never had foreign checks deposited, and now suddenly within a span of a few months, I'm depositing foreign checks on a frequent basis?

This is crazy . Ur exact situation (mezzi) I'm in same scenario. I literally just made 50k as well and am ready to send home. My brother works for IRS and told me bitcoin is used for like money laundering so that would def raise flags if u did it that way. He told me check is best way to go and make sure it's under a thousand evertime. And I think maybe drive thru with the check would be best option to avoid the awkwardness at the teller.  But like u said takes 3 weeks to get a check so it literally would take YEARS to get all my money . I'm in here looking for other option as well yall. Thanks