The question is not "should" you cash out, it's "how" do you cash out with minimal risk and expense?

First, consider where the coin came from in the first place. Did you buy it? Mine it? Do you have any records of where you bought it and how much you paid?

Assuming you are in the USA, you will owe taxes on whatever profit you made by selling the bitcoin. If you can't show how much you paid for it originally, the IRS will assume you got it for free and tax you on the whole amount.

Now, let's say you send 100 btc to Coinbase to sell and cash out. First, you can only withdraw up to your daily limit each day, and the limit starts at $3k. You can increase your limit by providing additional proof of your identity.

Now, let's assume you've been withdrawing $3000 per day into your bank account for the last couple weeks. Your bank is going to notice that you've suddenly got a bunch of money moving through your account. At some point they're going to freeze your account and notify the IRS that something suspicious is going on. Then your bank will contact you and ask for some explanation of where all that money is coming from. And they're going to want to see some proof. You need to be ready to answer those questions before you start cashing out. You might also want to tell your bank in advance about your plans.

Now, if we're talking about cashing out 1000+ bitcoins, talk to a lawyer.