I very politely questioned a few items on it, which made him upset.

I would group it in one and just itemize the expenses in QB and continue with your operating, savings, escrow accounts for LM and SD deposits. 

These "come with the package" and are part of the deal;  I do not get directly compensated for that time investment.However, when you are repairing something that a tenant broke due to abuse, or cleaning their vacant unit because they did not clean it as stipulated in our signed contract,  That does not make any sense.From a tax standpoint, that revenue I receive by doing it myself (and charging the tenant for my time) is taxable revenue, so I don't see where it is "double dipping" (which is what I think the courts sometimes claim).I have so fat avoided this issue by having the tenants sign a "move out charge sheet" that itemizes estimates on damages/repairs made (I apologize for the formatting issues). 

Can I itemize/label/categorize this money so the IRS knows this is for a rainy day?  

Based on some estimates I got, it could run $40000-$60000 just on these 2 items, without any of the build out costs.

If the building is built prior to 1978 has it been tested for lead paint (twice as important if there are children)4. do they have a trampoline or pool in the yardThose are a few items to add to your checklist as you do your walk through.

There were still a few small items to check off the list but, nothing that would prevent her from moving in or paying rent on time.

Each city is different, and some items follow state code.

I know you have to take the property as a whole and all look at all numbers, including location, NOI, Cap rates, future value speculation, Gross rent multiplier, etc, but is there 1 main item that you're looking for that helps you decide on whether to pull the trigger and purchase?

We utilized spring break to travel to the house and do what we could but had to hand all undone items to our contractor.