Photoshop Elements :: 1820 Field Map / Place It Exactly On Modern Map Using Two Reference Points

I have an old map showing a plan of all the fields that used to exist in this area.  It is just black lines and words.  I need to see through this plan and place it exactly at the right size and orientation using two buildings (which are shown on both maps) as reference points.  To do this I will need to resize and rotate the field plan over the modern map, anchoring the first farm point then pull second farm point to overlay on the modern map.  I will then be able to see how all the old fields sit in their modern environment and which old boundaries still exist.
 
Even making the white transparent leaving just the black lines of the plan would be a great start.The field plan is saved as JPEG and the modern one is TIFF.  Does this matter?