We made a good deal of money and I used the finances to pay off my student loans and get her car paid down.

I have been a student of real estate investing for the last 5 years and really hate working to make other people money (w-2). 

I had a court date last week where possession was granted back to me.

None of that really matters to me since the tenant is month to month and he would be gone once I took possession of the property.

My current strategy is getting student rentals until I have as many as I can realistically manage with the flip each semester and finding students.

Student rentals around UCONN is definitely worth looking into.I'm personally not a fan of wholesaling.

I am torn between cashing out this property and selling it to pay off lots of student loans and vehicle debt and another house flip vs keeping to continue renting.  

THE CA ASSEMBLY WILL VOTE BY MAY 31, 2018 Assembly Bill 2343 (Chiu) rewards tenants who fail to pay their rent or who remain in wrongful possession of a rental unit by delaying the unlawful detainer (UD) process by a minimum of three weeks.

Keep in mind the court officer's job is to make sure everyone is out of that apartment and you get documentation that the apartment was emptied and in your possession. 

Nothing replaces face to face at work and colleges make more money with on site students.