banks need to fill out a form if 10k+ of cash is deposited. if you break it up into smaller deposits to circumvent that, that's considered structuring which is also illegal and attract more attention.
big checks don't automatically flag any tax forms as far as i know, however in the event of an audit it will certainly attract further review.
MontanaRenegade86 did what i would do, document the acquisition cost, disposition cost and any expenses in the meantime to minimize your capital gains exposure.
if you have heirs you want to leave it to, it would be better tax-wise to leave it to them to deal with after you pass. they will get it at the stepped up basis for tax purposes and not owe a lot of capital gains taxes if they dispose of it soon after you leave it. consult your cpa or tax professional on that.
