It's the bookkeeping and phone answering that I struggle justifying.

You'll still have to do taxes every year, bookkeeping, an annual reevaluation of your portfolio, hire a small staff as you scale, etc.  

My wife has been a home mom (and my bookkeeper) for over 10 years now.

Then, I break up those crews and put the trainees (who are no longer trainees) on jobs to work by their self.That is the only way I get good workers who stay with my company.As for having a business that can grow, the number one most-important thing you need to do is to do all the bookkeeping and paperwork efficiently so that you do not get sued.

I agree he needs an accountant/bookkeeper, lawyer, and lender too! 

You have a separate tax filing, bookkeeping and payroll requirements and if you START as an S corp it's likely to cost you more in fees than it will save you. 

We used excel for a long time but now the bookkeeping is far beyond that.

Creating a company means extra costs (setting up a realistic business plan for minimum 3 years, registration fees, bookkeeping fees,..).

Any suggestions on the bookkeeping aspect of keeping everything organized?

I am a small landlord for now with a handful of properties. What software do you use to track expenses and income? Is there something specific to real estate investing or is Quickbooks the way to go?