My attorney actually advised against me buying the property through an LLC and selling the LLC (precisely because it does not avoid me paying transfer taxes in IL).

Your description of the process is precisely what the lender would do to "come after" your assets.

So, if you're in the 25% marginal bracket and your state/local taxes are 9% (for example), you should keep aside 34% for taxes.That said, this is tremendously conservative, as your marginal rate will only apply to your highest amount of income (most income will be taxed at a lower rate as marginal rates are on a sliding scale) and you'll likely have deductions that will offset some of the income.So, if you set aside this amount, you should have some left over come tax time, but should also be good in a worst case situation.If you want to be more precise, fill out a 1040 with your actual income and deductions after each project and see where you stand.

For those bills that are non-static, you have to setup the auto-bill pay at that companies website portal, like a utility bill for example, so that it can auto-deduct the precise amount of the bill for that month... your checking account billpay feature wouldn't be able to know that non-static amount, but its perfect for your mortgage.

Keep in mind that these policies are drafted by sophisticated attorneys and drafters and typically have precise language and exclusions.

Plus, even if the precision is false, it doesn't sound to the seller like you are just making up a nice round number. 

Same amount of money, but on a per unit basis, the cost is lower.To more precisely answer your question though, I've never bought a property in which i did not have a full rent roll and historical expense statement.

Part of this investing is hopefully learning what kind of returns are available for what types of investing and in which locations.So every question you are asking is precisely the type of data I was hoping to get from posts to this discussion. 

That is good to set the expectation and @Jim Cummings setting it up in the lease is really smart.Thanks @Kyle J. for the precise answer.

This is highly precise metric.