Now lets take a look at the history involving Kentucky Land Records.
Daniel Boone was hired as surveyor for the Transylvania Company founded by Richard Henderson in 1775. Hendersons intent was to create a separate colony. The Transylvania Company was ultimately deemed an illegal colony by the Virginia General Assembly in 1776 when the purchase of land from the Cherokee, In the Treaty of Sycamore Shoals, was invalidated. The land had been claimed by the Colony of Virginia.
Daniel Boone was to establish the Wilderness Road going through the Cumberland Gap to Boonesborough, the capitol of the Transylvania colony. Harrodsburg was established at this time and many settlers refused to recognize Transylvania Company authority. George Rogers Clark represented the settlement of Harrodsburg in opposition to Hendersons claim, as well as, Patrick Henry who maintained Virginias influence over that land.
Here is a map of the Transylvania Company. If it works properly you should be able to click on it to see the whole map which shows that the Transylvania Purchase covered areas around the Green River. You can find this map on wikipedia.
Looking at your Kentucky Land Records Commisioner Certificates for William Montgomery Sr., Jr., and John Montgomery it appears that all this land was not only bought through proper government channels from Harrodsburg, but the land lies on the Green River, extending westward into Kentucky flowing into the Ohio River. Many of the western counties in Kentucky were settled via military land transactions. At the time there was a lot of disagreement on land titles due to the Transylvania Companys grand plan.
It indicates that William Montgomery, Sr and family were not a part, possibly in opposition to the Transylvania Company. William Montgomery made sure to get a proper land record.
John Montgomery and Alexander Montgomery, sons of Alexander Montgomery and Martha Walker, were at Moores Station and Boonesborough. They fought in the Revolution under Captain John Snoddy, their uncle, who accompanied Daniel Boone to Boonesborough. They were the only Montgomerys at Boonesborough. They both lived in southeastern Kentucky on the Licking River in Magoffin County. This is the opposite direction of the Green River.
You probably already know that the Green River starts in southwestern Lincoln County. I say this because you mentioned Lincoln County marriage bond., later Bowling Green. These are western Kentucky areas. Specifically, the Settlement Certficate that mentions Green River includes Lincoln, Casey, Green, Adair, Hart, and Edmonson Counties. The Green River Military District includes Warren, Butler, Ohio, Muhlenburg, Hopkins, Davies, Henderson, Webster, and McLean Counties.
I hope this information helps.
Kay