I've talked to a couple of CPA's about this and I'm getting conflicting answers. 

Every couple of years I shop the policies and have not been motivated to change.

I know a couple properties managers at the shore but they dont have the best reputations.   

According to phone screening, a couple is legally separated (although they say they are working on reconciliation).

I'm guessing I should look for a decent job to support my self while learning with the first couple properties, but until then what can I do in the mean time to get the best start.I am working on getting some of the books so I have reading material this winter, but other than that what should/could I be doing?

Since last August when I took possession of the 20 unit, I began raising rents 2-3 units at a time, and now everyone is at the higher rents (average $140 per unit).In your situation it sounds like the rents haven't been raised for a while, coupled with your improvements the tenants expect there to be an increase.

Call a couple property managers in your area and ask what they think it would rent for.Finally consider that while your agent is probably a good and honest person they are incentivized to give you the high estimate and not necessarily the most realistic estimate.  

Do you get guests who are unhappy/ leave bad reviews if they are charged $100 to check in a couple hours early?

I have a couple of potential off-market deals coming my way, and want to partner with an experienced local investor for every step of the process...help with analyzing the deals, as well as the rehab.

Month two we heard everything from he was getting a sign on bonus, collecting a debt, to the check got lost in the mail.