Cosmetic repairs interior/exterior, and getting tenants in.

Cosmetic updates to interior and exterior.

With some cosmetic improvements to each unit I expect to be cash flowing 1200-1400 per month...

Furthermore its first two units are great and can be moved into, the top unit needs some modernizing in terms of cosmetics but other then this is fine, i also will ensure to have it inspected and collect a report along with my due diligence. 

Most of the units just needed a cosmetic update to bring them back to life.

Put about $9K into the renovation, full cosmetic job, new flooring, new kitchen, new bathrooms.

Your neighbor has no responsibility to do this, but it is worth asking in case they want to cut it at the tree for cosmetic reasons.

I'm not about to increase his rent because I know I would have to make cosmetic updates to the property if he left and even if I did rent it for market rent, the new tenant may not stay beyond their lease term (net-zero; 1 month of vacancy after 1 year would equal the entire additional rent revenue), may not pay reliably, and may cause damage.

for the siding, is it a few pieces and even then, it is cosmetic or a sign of a bigger problem? 

we have a contractor going in to do cosmetic work and some minor repairs. we plan on renovating one side in a two month period time frame.