The tenant may voluntarily agree to leave in exchange for a cash payment or some other benefit, but you cannot make her leave unless you were completely removing the building from the rental market under the Ellis Act (and I am not as familiar with those rules to know whether it would work here).So, with all of that said, if the deal depends on this tenant vacating the apartment (which, if she is paying $350/month rent, it probably does), then I would only move forward if the seller will agree to deliver the unit vacant at close of escrow, OR, if you can obtain a signed agreement with the tenant to move out for payment (and for that agreement to be upheld, the tenant should probably be represented by a lawyer).  

A real estate attorney should be able to assist you with the documents required to complete the transaction.As it relates to the end payout, it all depends on your contract you have with the seller. 

If you negotiate a good enough deal that pays you then complete the transaction with the investor to buy the house you have under contract.

I'm Shane, a complete newbie in the Cleveland area.  

I'm a complete newbie to the real estate game, who dreams of starting my own residential real estate empire, buying and holding homes across the country in consistent markets to generate passive income in order to be my own boss. 

It does not matter to me one bit if they are working in this market or elsewhere in the country, I simply want to learn and be exposed to the highs and lows of the business. 

Should I have the bill sent to the rental and hope that the tenant pays it or should I simply pay it myself and add the average tothe monthly rent?

I'd love to help you but completely understand if you want someone intimately involved in those towns specifically.:-)

I know that I will completely take advantage of that person in the negotiation process since they have zero clue what is customary and to be expected in the process.

I'm a complete newbie to the real estate game and currently entrenched in the education phase of investing.