We're looking for a more scalable, software solution.

I am a software engineer and my wife stays home with our kiddos.

I currently rent in Manhattan, where I work as a software engineer.

@Steve Bergeron Are you a home developer or software?

You can also buy lists from companies like list source and there are some REI software companies that have a cash buyer search feature.Some of best ways to find motivated sellers is to purchase lists from companies like listsource and or compile lists from city and county like 60-90-120 days late on mortgage, pre-foreclosure, delinquent taxes, water cutoff, code violation, probate, divorce, evictions for tired landlords etc.

Instead of spending a bunch of money reconfiguring the property, here are two better ideas for you:1) Get a new property manager2) If you don't want to go to the effort of splitting the bill, figure out what the average cost is for the year and charge it back as a flat monthly fee that is automatically added to the rent by the property managers software every month

@Hiren Patani I second the Michael Blank software.

I am a 39 year old software engineer, looking to get into rentals and whatnot.  

@Jared P.Quickbooks is an accounting/bookkeeping software that is used to track your data(income/expenses/assets/etc).If the property types are organized in a separate entity type, I would have them in two separate files.If they are not in a different entity type, you may want to use the "class" function within quickbooks to distinguish the asset classes.With that said, you may want to still operate them in two separate files if you find it that both businesses are too unique to another.

There is "what if" software made available to mortgage people like myself.