Also having two mortgages will also give you a good tax deduction on your Schedule E at the end of the year.

I'll eat the taxes.Another option would be rolling over your withdrawal into a self directed IRA that you can use to invest in properties.

If I can't do that then I need to add a buffer to every bid to cover the ones that I end up eating some costs. 

They'll have enough leftovers for me and my wife to eat for 2-3 days. 

That expense can eat at cash flow, but it's also a high value to have, as it can take a lot of your time.You may also want to figure out what your 5-10 year goals are for owning, as you are limited to 10 financed properties each.

I have a lot of questions and as I believe David put it, I'm in sort of a conscious uninformed stage. 

I would honestly spend the next several months eating ramen and making sure every dollar of debt is paid off and just pile cash into a high yield savings account.

I'm curious if there's the potential to instead use the money to go towards the purchase of investment property, cost segmentation, and accelerated depreciation vs. just eating the tax bill.

Same with what they want to drive or eat.

Once you do more creative financing you'll be able to buy properties with none of your own money down and pay less of the compounding interest that eats away your cashflow less as you pay the properties off and have les debt to pay interest on.