You are probably better prepared than most and I wish you best of luck.

By reaching out to the city beforehand, you can ensure that you are prepared for the renovation process and avoid any potential complications that may arise.

Be prepared to make some visits to the city after you make your purchase. 

Can someone give me a checklist of some sort that would help me on my first rental property to make sure am as prepared as I can be?  

You may want to consider working with your tax strategist remotely to expand your options.I would also recommend looking for a tax strategist who is willing to work with you throughout the year, not just when preparing your tax return.

Whatever you decide to go with, if you go cheap just prepare yourself that you'll probably never touch it up well unless you have a leftover can.

An estoppel certificate signed by every tenant stating they are in a month-to-month tenancy at how much rent, are they current, amount of security deposit - even if the amount is zero it needs to say that.Tell them now because these will take time to prepare and then the seller has to get the tenants to actually sign them. 

Are you prepared for vacancy loss, taxes and insurance to go up next year, etc? 

I've been reading a lot about business books, negotiation books and I seemed to had an analysis paralysis because I felt very stuck even though I am learning and preparing.

Plan on this being a live in renovation, ultimately preparing for the fall semester in August when tenants would move in.