With that being said if you're using an esig software we are talking about a few clicks why not just do it the long way to be safe. 

I'd probably use local realtors to help re rent any vacancies and then possibly use a PM software like rent redi to keep everything in one place.Has anyone had management in place and then decided to opt out to self manage?

Yes, definitely reach out to an accountant for help with an LLC, an IRS EIN, accounting software recommendations and tax planning. 

Then after that split is taken out, we pay income taxes to Uncle Sam, errors and omissions insurance (in case there's a lawsuit), Realtor's Association dues, MLS fees (so you can look at properties on Zillow), monthly technology/desk fees to our broker, health insurance, car insurance, gas, maintenance, clothing, computer, cell phone, software, marketing, etc.

I would check out Hospitable for property management software that does a lot at a reasonable price!

If you are using accounting software attach the receipts to the transactions as well.

What are some of the best accounting software programs that you have found for handling the rental finances?

There is a software that can help determine the true value of the old roof costs that are no longer present, especially if a cost segregation study was not done previously. 

You also can have someone who uses matterport or other software to scan and create floor plans if that’s all you need and that costs like 250

It's certainly not easy, even when using all-in-one software like Appfolio.