Having worked, trained and coached property management businesses, I think much of your review is valid - especially the work order elements. It's not about (as some of the other responses say) being a crappy landlord or ignoring a small fix that turns into a ten grand piece of work - many tenants (maybe not you, dear reader, but when you have a rent roll of hundreds or thousands) do make inane requests. These aren't so much maintenance things as requests - now that I've signed a lease for this cheap house, can you install air-conditioning, build a fence, and re-do the bathroom, and I'll approve a $10 rent increase at the next renewal.
Your response to other elements contacts, tasks, and automated rent collection says to me that the product isn't designed for you. When I've got a team of 4-5 property managers, 600+ properties, some on fixed leases and some on holiday letting schedules, time lost to paperwork is enormous. Actually, I've not worked with an office that hasn't had some sort of technology for contact and property data; managing work orders, automating payments, assigning tasks to other managers are all fairly common now as well (and I see other key selling points in the product, so that's not to be taken as a criticism for 2 years' work).
Your response to other elements contacts, tasks, and automated rent collection says to me that the product isn't designed for you. When I've got a team of 4-5 property managers, 600+ properties, some on fixed leases and some on holiday letting schedules, time lost to paperwork is enormous. Actually, I've not worked with an office that hasn't had some sort of technology for contact and property data; managing work orders, automating payments, assigning tasks to other managers are all fairly common now as well (and I see other key selling points in the product, so that's not to be taken as a criticism for 2 years' work).