If the rough estimates for 2018 put his income at 80-100k then 20-25k in federal taxes seems to be on point - unless he's been taking massive deductions to get his AGI (adjusted gross income) down. It would be hilarious if he revealed to us that he's written off like 40k in expenses, because the most expensive deduction I can think of is his second internet line and the fraction his office space takes up in square footage.
He's never provided proof that he's on hard times, and you'd be right in that he's purchased so many expensive things. However, with his income he likely has qualified for some very generous lines of credit. He's taken all of this play money out at 0% interest and now his creditors are pulling out the harpoons as his intro 0% rates have expired. The only thing he's said before is that his minimum payments have doubled. Either the intro rates are done, or his credit score is tanking and variable rates are going up. Regardless, it's always in his favor to say I'm in debt and need money so none of this ever really matters.
He'll make his credit card payments and get his balances down but at the same time pile on other expenses like the Space Needle visit. I don't think he's ever made a full effort to save his tax payments up front. He's just been living off a minimum payment lifestyle with a dash of ~$1500 CT condo payments.