Once I upgraded to pro the itemization of repair cost went away...

What items do you think could be missing?

I needed a contractor to estimate the costs of some of the items we plan to do and help us decide which things we'll do ourselves vs what they charge etc.

If they commit to signing the Lease Agreement within a specified period (usually 30 days max), I convert this "Holding Deposit" to the Security Deposit (fully refundable, minus items above normal wear/tear).

BTW, my monthly expenses are all encompassing - any mortgages + insurance, taxes, vacancy allowance, capex - but not taxes, since those are (largely) offset by itemization.

James,You will also want to separate out "standard of living" items from "unhabitable" items.The landlord isn't responsible for thefts, vandalism, or the neighborhood going down the drain...He *is* responsible for major pest infestations, heat in winter, a plumbing system in good repair, getting rid of pre-existing mold, etc...

If there are things you're weak on you should consider finding partners to help you with those items.  

This way all specific systems that could cost big $$$ are getting evaluated by the people who know them ( and the plus side is we are getting prices to fix items if needed).  

I fixed up a 3bedroom/1 bath house that was had it's plumbing and AC stolen and the bathroom floor rotted out and I couldn't have created 100 GL entries without breaking out every receipt at a line item and every trip by itself. 

A couple items I learned...The contractor we used had to already be approved by HUD to do the work.