The issue is that there is no way to associate my local or state business sid w/ the VRBO tax payments and VRBO does not have a way to give me confirmation of the payments like canceled checks or draft receipt. 

the great thing with real estate is that the IRS gives you an annual deduction called depreciation which is a non-cash tax expense.The second thing is timing of expenses, the IRS may allow you to accelerate many expenses in earlier years as opposed to over a longer period of time.The third is that many taxpayers miss out of deducting all the expenses - They just write off items that are directly related to the rental(insurance, taxes, interest, etc) without factoring in personal expenses that help your rental business.If you purchase a bunch of cost friendly houses(below $100,000) and are getting close to the 2% rule, then it is likely that you may have positive taxable income from your rentals.Best of luck

@Derek Sperzel, If you and your wife file a joint tax return then you and she and those single member LLCs are the same taxpayer (as long as the LLCs do not file their own tax return). 

-Buy and Hold (houses)- buy a house, rent it out to a tenant and use their rental payments to pay down the Principal Payment + Interest Payment + Tax Payment + Insurance Payment.

Counties and cities want to post bonds because of last downturn the roads on failed projects went unfinished and they were stuck with finishing out roads at taxpayer expense.You didn't mention topography of the land.

@John Hugh, Even though they are the same share holders, LLC A and LLC B are two different tax payers. 

You also need to be saving for insurance and tax payments. 

So the longer you defer the more money you'll make off the govt's money.And you've also identified a good way to get out of the landlord gig and still keep the use of the deferred tax for your benefit - a 1031 exchange into something passive like a DST.Any tax paying entity can do a 1031 exchange. 

So it would do you good to see what your total monthly pre tax pay is compared to all of your recurring monthly expenses (credit cards minimum payments, auto loan, etc).

Backed by the tax payer!!!