Build the secondary units and legalize them, then refinance with them in place.

The dilemma i have is that I can’t decide if it makes more sense to embrace the c class identity this property gives the impression of, or put a lot more into the renovation, get better quality tenants and convert it to the B class property that the building (and the area) should/could be. 90% occupied, the yearly rental income is around 600k with 420k NOI. 

Partner Driven added value to the Powder Branch Rd deal by investing $35,619 in comprehensive renovations.

What made my investor interested in this deal was being a corner property you are able to build a full 3rd story addition by right which would massively increase the value of the property with similar 3 story properties trading in the low 600k's.

Partner Driven added value to the Oak St deal by investing $67,150 in comprehensive renovations.

The first step to building your REI empire.

By putting 10% down I probably will be less than breaking even every month ((like an extra $800-900 per month at very low/conservative rent prices)  with the building fully tenanted (as is condition not counting value add with renovations). 

You really want a rookie putting a waterproof seal on the top of a building?

You hardly build any equity in your first year, it makes sense to refi only if the rate is substantially lower or if you can get rid of mortgage insurance.

I wouldn't rely on information here as we haven't seen your building nor understand your bigger goals but this is not something I ever recommend my clients to do....even if they have a few deals under their belt.