OP, is there a strong reason you want to live in Brookland? It's a perfectly good neighborhood, but if don't get in to a charter you will be looking at $50k+/year for private school. Seems like it would be much cheaper in the long run to just move into a neighborhood whose DCPS you like. Or are you not considering DCPS at all? I know upper NW isn't everyone's cup of tea, but you could still live in Dupont, Georgetown, Glover Park, etc. and have good DCPS options.
Hopefully you will get into IT and all will work out!