Here a few obstacles I have:1) My first year paying out taxes on my ordinary income, let alone for the 401k withdrawal.

What should I  look for out of the ordinary?

I would say credit unions are probably out of the question there is a Community Bank i use that is known to do out of the ordinary type loans.

I am creating a one-page reference document that has emergency numbers, how to report ordinary maintenance vs. emergency maintenance, how to shut off water or electric in an emergency, instructions for replacing the air filter, etc.

I was told the difference is really how one is being taxed as ordinary income vs capital gains.

The tax on unrecaptured Section 1250 gain — the portion of gains on depreciable real estate (structures used for business purposes) that has been or could have been claimed as depreciation — is capped at 25%.Most other investments are subject to a preferential rate of 0%, 15%, or 20%, depending on the tax rate that would be assessed on the same amount of ordinary income.There may be taxes in addition to the tax rates shown in the above table.Taxpayers earning income above certain thresholds ($200,000 for singles, $250,000 for married couples filing jointly) pay an additional 3.8% tax on all investment income.[3][4] Therefore, the top federal tax rate on long-term capital gains is 23.8%.[5]

@Daniel Dietz, Think of the 1031 as a sale of investment real estate by a tax paying entity and the purchase of replacement real estate by a tax paying entity. 

One year of that is just holding it a year to be taxed at capital gain 20% versus ordinary income at 38%.  

@Jack B.Everyone's tax situation is different and for that reason - the title company will not withhold federal/state income taxes on your behalf and remit them to the federal government/state.One thing you may want to look at is if you are required to make estimated tax payments to avoid having to pay a penalty.Your accountant will be able to answer this question.

This depreciation will be recaptured as ordinary income at your marginal tax bracket rate or 25% whichever is less.If your marginal bracket rate is 15%, then the federal income tax on the sale of your property could be around $1850.