To get the benefit of taking your STR losses against your other ordinary income (and a cost seg would help to increase the loss), I think you want to make sure your average rental period equals 7 days or less, and that you meet material participation. 

What should I  look for out of the ordinary?

Oren, your procedures and ordinary customs are different there (LOI's, sign-backs, etc) so we may be a little off.

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

When it come to short term capital gain, there is no standard , it will depend on your income level as it be treated as ordinary income.

It is 27.5 SL depreciation that is allowed and therefore there will not be any depreciation recapture taxed at ordinary rates.

Your lenders will pay ordinary income tax on the Interest they receive, just like any other interest they earn from bank accounts, CD’s, bonds, etc.  

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

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

If repairs or restorations are for ordinary wear and tear, then the landlord must pay for it.