Expenses like this include things like property taxes, insurance, maintenance, administrative and office costs, payroll, marketing expenses, and property management fees. 

So, both my wife and I are full time W2 employees and are in the 24% tax bracket, and I came across the short-term rental loophole which sounds really amazing for taking write offs and using them to reduce your W2 taxable income, but also equally difficult to qualify for, unless you are within a short driving distance to your property.  

Assuming that minimum, I would only be spending about $250 a month on average, which comes out to $3,000 a year, with $27,000 left over (or 25,500 after taxes, assuming I contribute about $5,000 to an IRA that year, which I full intend on doing) for the above. 

We want to buy a single-family home as close to debt-free as possible and then use leverage after that point.

Nor would I buy here with the looming property tax threat against STR's. 

If it is to play it safe and have a feel for the type of actual operating income that the property can produce before you put debt on it, that's a safe and solid idea.The good news, however, is that you're likely going to be purchasing a furnished property.

LLC or not won’t make a tax difference. 

My numbers are kind of tight on cash flow due to a blanket loan (had to do to pay off lots of debt/rehab). 

I am happy to speak to what I have seen as the most common set up from a tax perspective to give you a starting point for a deeper discussion, but ultimately you will want to speak with your CPA in conjunction with an asset protection attorney because this requires a deep dive into your specific situation.  

Payoff as much outstanding debt to get the DTI down.