Use conservative assumptions, outperform on them, and watch your investors grow your network for you by way of referrals.Give the best reporting in the industry. 

First the assumption that bruised credit= late rental payments is simply not the case.

My assumption is, unless you have him already, contractors are not usually willing to jump from their jobs to go quote projects they won't be getting.

After that the real estate market follows, but much slower.The net effect is that the down payment you are sitting on now invested in stocks and mutual funds takes a bigger hit than the reduction in RE values, making it much harder to buy the same property you could have bought today.There are a lot of assumptions baked into that statement, like that you have a chunk of change in the stock market, or that you even have a sizeable down payment.

Now, the core of your question relies on the assumption that your contractor is out to take advantage of you. 

So basically I'm going over what he sent me, I started analyzing the Schedule E that has my 3 rentals and noticed the total expenses are WAY lower than what I gave him on my reports, so below I give you the example of one of the rentals (all 3 have the same characteristic, my accountant has expenses WAY lower than what I sent him on my report):House 1 - long term rental - Schedule E (house bought in 12/2013)   Income: $9,346   Expenses declared by accountant: $9,992 (this is what he somehow figured out)   Now on the report that I gave him my total expenses are $30,300 (repairs $11,792, supplies $8,329, the rest were renovations and other stuff), so there was a lot of work on this property.I asked him why the difference and his response was:"I made some assumptions in the earlier years about capitalizing costs vs. repair costs. 

@Ryan Johnston Network as hard as possible and do not make any of the assumptions on estimates on cost that you made in Chicago. 

@Roshan Taheri If rental real estate income does in fact qualify for the pass-through deduction -- and there is no chapter and verse on that although most practitioners are operating under the assumption that it does -- you will get the deduction regardless of whether you hold it in your name or through an LLC (as long as the LLC has not elected to be taxed as a C corporation).

I try to make a fair set of assumptions and figure something that would work for both of us.

Your assumption is also correct where you are better off finding a property that has value-add such as Rehab and increase in rent- as a Rehab will lead to lower maintenance and capex costs