Software development is slow.

I don't know how to run a skip trace and don't know the proper software that people use and in Florida, some people do not take kindly to knocking on doors :)Thank you!

You can look into the BiggerPockets-affiliated software for landlords here in the Tools section.Another option could be a local Realtor who either works a ton of rentals or does a lot of business in North Austin.The software route may still require involvement on your end i.e. setup, communication, document review, etc. 

For context, I'm currently doing research on property management software, and was hoping to learn more about the challenges that landlords face.

What property management software you guys are using, and how much are you paying for it?

Check out Antoine Martel, he has a software and coaching program called Flip System where they hand hold beginner real estate investors through the turnkey process they have completed over 1000 times.The process is typically stressful, teams on the ground are hard to assemble, there are many simultaneous moving parts, and time and capital invested isn't guaranteed to generate a return.

Most PMC software is set up for electronic rent payments by tenants that automatically updates rent ledgers. 

Other ways (off the top of my head):- Dedicated Revenue Manager on top of dynamic pricing software- 24/7 guest support- Vendor discounts (i.e. roof replacements, AC repairs, etc)As a new PM I think it is important to highlight where you add value instead of battling on price. 

What are some features in property management software that are absolutely vital?

I collect fees and rent with Baselane and tag each security deposit in the bookkeeping software and leave a note on which tenant it's for to avoid having separate accounts for each deposit.