I ask these because if you really want to make this a long-term investment and are ready to take on the extra work (software makes it easy to automate about 80% of this, but you still need to be prepared),  then I wouldn't rush into this just to save on taxes and purchase wrong. 

Use door loop or other property management software don't build this yourself 

It's still important for each individual to test the software platforms to see which one they prefer.

I feel as I'm expanding that having an accounting software to track/categorize my expenses would save me time.

To address this: Audit Expenses: Drill down into each expense category per property.

I asked her where the higher cost was coming from, and she left it vague and said it was time and materials based.I asked her via text if I switched to self pay, if I could bill my insurance on my own later, and she said “We would wait to submit to insurance on the proper software - it won’t be broken out the way they prefer,” which strikes me as strange since it seems like the insurance and I should get pretty similar information or invoice breakdowns.

Here’s an excerpt (see below) from the IRS Audit Technique Passive Activity Guide on this rule, which covers more than just the 100 hours. 

Reach out and I can share the contract writer software.

What softwares do you use for your team if you don't mind me asking? 

Quote from @Sameul Ahsan: PMS softwares normally collects and we also have that info.