Highlighting cells according to dropdown list and date

Hi,

Ok so I've been trying to do this but haven't been able to, so maybe you guys can help me here.
In my job I have to receive documents periodically (monthly, every two months, every 6 months, etc.). There is also a yearly deadline. In front of the table below I have a month table (Ag/18,sept/18 and so forth)

Example:
Account__Start of Date___Deadline______Frequency
__A______1/8/2018_____3 years_____every 6 months
__B______23/5/2017____5 years_____every 3 months

Want I'm looking for is to highlight the months I'm supposed to receive the documents using dropdown list of frequency so that they will automatically highlight the given months starting from the "start of Date" field.
So, in Example A, as I fill the info it would highlight every February and August, for 3 years straight.

Is It possible??

Thank you guys for any feedback