Why not use Cozy.co, which is designed for this and free?  

For me as a PM- feasibility, concept, design, plans and specs, permitting, contract negotiation, and construction administration.

I already have some design ideas in mind, hopefully making this process less bumpy.

If its officially designated historic that can get very complicated in some locations. 

While our apartments are not designed to attract the cream of the crop, do I create a criteria that demands better, or just be a little more loose and general?

We put A LOT of effort into our designs and we’re passionate about rehabbing and creating HOMES not just houses for margins!

They even have several off-the-shelf designs that fit the narrower & deeper lots you often find in the area. 

Should I look to hire a designer/architect for this?

Does the cost of designing, and adhering to historic guidelines outweigh the tax credit benefits.

I forget the name of the program, but basically it is designed to prevent the IRS from issuing a fraudulent refund after they inevitably receive fake tax filings next spring and it should keep your filing as the only one they actually process.