I have seen they have been pushing RentRedi a lot on the podcasts lately and I fell victim to their marketing tactics and checked them out.They seem to have fairly reasonable plans ($9/month for year plan) and offer a variety of features but I am still confused why someone would pay for property management software when there are so many free alternatives out there. 

BTW, been doing software development for ~30 years. 

It's a good place to learn more about servicing software and meet vendors, too.

I use Hospitable and a number of other softwares for automation and efficiency.

My profession is software / web design and I am interested in property management and using a property management type software.

Here are some things to consider:Most investors don't need software until they have 5-10 rentals.

You can do a lot of the projections you're talking about in financial planning software, like estimating RMDs. 

This generally includes anything with a useful life of 20 years or less such as software and computers, equipment, specific building improvements and office furniture.When to consider bonus depreciation?

How much is your annual spend on 3rd party software and apps?

My team also developed software that scans national MLS listings to identify the most profitable STR properties which may be of some value for your search.