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.  

The only item we are concerning is the property type. 

Subsequently, we just received a notice of violation with the Chicago Department of Buildings that list a handful of exterior items and mold in that same tenant's apartment (which they were not able to verify because the tenant wouldn't let them in).

This is the first item I'd like advice on (HELOC or refinance and take out cash.

Both Quicken products do income and expense tracking for a Schedule C type business and allows TurboTax to import tax items directly from the Quicken database.