Orrr I could sell it and get about $150-160k in cash to invest in in stocks or in a larger property closer to my current residence.

Would either of your rooms allow for a bed larger than a full?

Very saavy for you to stay in the studio and rent out the larger portion.RentRedi should get the job done for tenant screening.

They were major drama queens, I fixed their cars, fed their dogs, shuttled them around etc.

I am much more into forced equity and getting into larger projects myself, but I live right here and have built an excellent team around me.

Why can't you start with some smaller residential or small multifamily commercial properties to get your feet wet, show proof of concept and possibly try to take on larger deals.Or possibly find a local syndication group and become an employee under them learning the trade and finding a mentor in the space.

If you think that you can generate a lot more cashflow relative to the amount of equity in other investments, then I would consider selling and doing a 1031 exchange into larger property(ies). 

With larger portfolios that could be reduced per property.  

We took over the property management because the owner was having multiple issues with a few of the "tenants" that have illegally sublet the property, and we are now dealing with the ripple effects (e.g. squatters, dogs, dispute with neighbors etc.)The landlord is cash strapped, and has asked me to go in on the property/deal with him in order to get a cash infusion to cover legal fees & renovation costs. 

For capital expenditures they tend to be larger so getting that fund growing from the start is important to maintain stability.