IC+Cobra Health Insurance=Deduction?

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Itssalsatime

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[EDIT] not sure how to change the topic title, but I wanted to change it to Filing IC taxes..

My wife and I are paying quarterly taxes. I am a stay-at-home father and she is an EM, we live in TN (no state income, so we will deduct sales tax) We do not have a SEP-IRA yet. We were going to form a living trust with a lawyer along with a will, but he told us forming a living trust is pointless until we have equity.

Here is the breakdown of our current situation:
$6,000 in our checking
$28,000 in our savings, but that money is from the "side" escrow account we got at closing [home] from the sellers, between their lawyers and us, with wording in the contract that says it is for home repairs only.(which is what we are using it for, we purchased a home with some damage)

August 1st 17'- Dec 31st 17' Hourly Wages = $146,000
Signing Bonus = $24,000
We did not file in September, because we did not get first check until 09/25.

We have been paying $1,700 a month for Cobra Health insurance since September 1st, which I was reading is deductible. ($6,800 paid by dec 31)

HUD deductions:
loan origination fee of $999 and property taxes of $5,448.63 and $119.74 of prepaid interest.
Have contributed $7,000 to church missionary not-for-profits
Have paid $36,000 mortgage interest ($6,000~ month)
$12,000 new car taxes
Hundreds of receipts with easily $2,000+ in sales tax on them
We have 1 child (another due in Feb, then we are adopting several next spring) - I think we are phased out of this?

Total Deductions=$63,367
AGI= $106,633 For the year 2017 (the first part of 2017 was W2 employee in medical residency)


$14,758.75 plus 28% of the amount over $75,950

so we were going to send in:
$16,314 Self Employment Tax
$14,758.75
$8,591.24 ($30,683 x .28)

TOTAL: $39,663.99

Am I missing anything?
Did i do something wrong, like the self employment tax??
Are we really paying ~37% tax?

I have an old trading friend (I used to be a futures trader) who said my wife and i should open a TD Ameritrade account for $1,000 and he will "Explain why, Tomorrow"... Not sure what he has in mind.

thank you kindly.

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