I would ask him for output now based on whatever software he uses even if it does not have all the elements you want that should be easy, then set a timeline for getting the rest.

Thinking about something other than spreadsheets for 1 Short-term Rental and 1 Longterm rental with plan to add more longterm rental.  Recommendations please.  I basically just want to use to track financials for me a...

What other software do folks use for short term rentals?

I’m trying to find a cost effective (or free) property management software.

Hello All,I am searching for a suitable rental property management software program to do the following (and whatever else I have missed);-Record financials that I can use for tax time (including expenses outside of rent and such).

It sounds like this functionality just isn't worth fighting for in these software's.

I just don't want to spend hundreds of hours on this project as that alone would nuke ROI (I'm a software dev, my hours are expensive). 

Keep in mind that I intend to continue to work as a Software Manager for the next 3-5 years.

I’ve never done anything off-market yet and my only frame of reference is signing papers for my realtor through their software of choice.

Utilizing a property management software that has that feature built in is a bonus.