However, if I sell I will be losing out on possible appreciation and paying down the mortgage.

Also tenants that carry re insurance know not to f* with your property because they might lose their insurance or get higher premium next time as more and more landlords require it nowdays.

Do you have enough disposable cash to cover the $600 you will lose renting the property plus enough cash to cover the fees associated with the refinance?  

My criteria is mostly west side of Cleveland and Parma but I am willing to venture other areas.

Because if I don’t get the original $2,000 back, I don’t understand who in their right mind would risk losing that much for only $50 with some interest if property owner pays it back.

I know that I have to go for the cashflow so I trying to don't go wrong cause is the first deal and I don't want to lose money, and I know that the first deal is the more difficult

Also, I do not intend to live on any of the proceeds of my real estate ventures and hope to aggressively grow the portfolio in the next 5 years.

Using your numbers and refinance you show you are making $22 a month but in reality you are losing money. out of 4 months you receive $975 and your expenses are $720*4=$2880 plus $200 insurance and $400 taxes. 

I really want to get into RE and I was thinking starting off wholesaling but Losing motivationAnd now just thinking about getting my real estate license in Arizona.

My wife is the PM, if I show up with a building full of tenants she wants nothing to do with I will lose my job-or worse!