On a more enterprise scale, I employ RevMax software as well as a fractional revenue manager who looks at the prices daily on a market level and a comp set level. 

The simple reason is that you cannot even tell debit cards from credit cards without a special software.

I have ~20 doors in OH that I self manage (there are some awesome softwares out there now for self management) and am looking to start investing in Buffalo too.

They/you can't choose the carrier - their software assigns it.Fortegra is one of the carriers (paper in insurance parlance) that their product is written on.That said, Fortegra is A- rated I believe by AM Best so that isn't the issue.I'm going to take a guess and say that your umbrella is written with PersonalUmbrella.com (Markel) and they require all underlying insurance to be A-rated but also with an admitted carrier. 

Whether you need a CPA with just three rentals depends on the complexity of your situation and your comfort level with DIY tax prep.If things are pretty straightforward, you might be fine with tax software for now.

Never used software.

I created KBKG's Residential Cost Segregator software.

Our software has an option to have someone who looks at our pricing daily and tweak yes. 

Does anyone have any tips or software tools to help give estimates on pricing and the potential occupancy of the rental?

I have a LLC set up, and property management software ready to use.