I don't enjoy bookkeeping/ taxes)I kind of feel like the main reason I need PM cloud software is for basic online rent collecting and setting up that system.

You'll learn about persuasion, presentation, negotiation and marketing and enough about bookkeeping to be able to find a CPA later, and it will help you be an even better real estate agent.Even if you only knock out 2-4 classes a year, you will eventually finish, and it's an important checkbox to get your resume read if you ever need to pick up additional income or benefits with a day job.  

I explained to him we will need a team, not just him and me, but a CPA, Lawyer, Book Keeper and contractors/handymen as well as an agent.

No you aren't out of line but for non-commercial multis (1-4 units) sometimes the owners just don't have good bookkeeping so that just means you will have to estimate revenue and expenses...if you want solid financials you'll have to play with the big guys/gals in 5+ multis which are considered commercial...you're in mom and pop residential world right now ;)

The bookkeeping is a little weird right now, because I'm paying myself rent, and the tenant's rent is below market value (and will be until May).I wasn't able to find any deals on the MLS that met my criteria.  

Megan,I am a virtual bookkeeper, so I spend a lot of time trying to find out what potential clients want in a potential bookkeeper which happens to be similar to what they want in a CPA.1.

@Robert CaturanoMost multi-family property owners should have some sort of bookkeeping/record keeping.

I make decisions about when to evict, when to raise rent, and do all of the bookkeeping on my own.

If you want to get that big you have to find a way to remove yourself as the bottleneck and have systems in place so that things run without you in the picture.The things that I find bogging us down, preventing us from doing the important things like finding money and deals, and that I plan to hire out are:-Day to day phone calls about Maintenance, Rent payments, Lease questions-Listing and showing properties-Drafting & signing leases-Generating and mailing/delivering 7 day notices-Entering bookkeeping into Buildium-Water billing-Occasional Bank Deposits-Occasional other errands like dropping off checks or materials to contractorsI think the first one will be the toughest, as I never know what will be on the other end of the phone line and many questions I get require discretion and careful handling.

Ask him for his rent roll/bookkeeping for the past year or 2 to verify that these tenants are actually paying this rent.