Tibbie Fowler sought and found

Tibbie Fowler o' the glen, there's ower mony wooin' at her
 Wooin' at her, pu'in at her
Wantin' her, canna get her
Silly elf, it's for her pelf
A' the lads are wooin' at her

The Logan family had a long  history of association with the Scottish Crown. A Logan had accompanied the “Good Sir James” Douglas on his ill-fated mission to the  Holy Land with Bruce’s heart.  By 1382 the Barony of Leith had come into their possession.   Good and bad, they  ruled over the port and the neighbouring estate of Restalrig until the early 16th century by which time the lands had been divided amongst three branches of the family.  Sir James Logan, Sheriff or “Shirra” of Edinburgh built his mansion where St Thomas’church stands at the top of Sheriff Brae. The church is now a Sikh temple

Tempora mutantur, nos et mutamur in illis

The catastrophe of Flodden and subsequent, ill-judged political ventures brought a decline in Logan fortunes until, in the late 16th century, Robert Logan “ ane godles, drunkin and deboshit man” had lost his Restalrig lands to pay his debts. After his death, he was accused of being implicated in the Gowrie conspiracy and the family were outlawed and any remaining lands confiscated. Some of their lands in Berwickshire were later returned to them and the  sentence of outlawry revoked.
Respectability of a sort returned to the family.  Tradition has it that George Logan, a grandson of Robert, married “weel tochered” Isabella Fowler and, with her large dowry, built a mansion at the head of Shirra Brae where he could view all the comings and goings of  Leith harbour.

Isabella was the daughter of  Ludovic Fowler of Burncastle near Lauder.
Burn Castle stood overlooking the Earnscleugh Water  near to where one of the branches of the ancient Herring Road  wound its way from Dunbar to Lauder. Of the castle nothing remains except the name of the farm on the site.

The Herring Road - Burn Castle stood close by

Another version has her as the daughter of a portioner or the owner of a small portion of land at Lochend, now a sprawling housing estate. Lochend House built in 1820 incorporates the gable end of the old Logan stronghold, Lochend Castle.

Lochend House

I think this is less likely given the amount of money needed to restore the Logan fortunes and  rebuild on the old site of Shirra House.
It seems to be the old story of the nouveau riche buying their way into an ancient family name.
One can imagine the folk of Leith, who had not always benefited from their Logan superiors, having a good laugh in the taverns along the Shore as the wags sang their comic songs about the newest lady of the house with her jewels and high heeled shoes and attempts to overcome the deficits of nature

The Shore

She's got pendles in her lugs, aye cockle shells would set her better
High-heeled sheen wi' siller tags and a' the lads are wooin' at her

This must be the Tibbie of the satirical song.

Wilson’s bonny Tibbie Fowler’s five hundred pounds  might have bought a coastal trading boat (blog 30th Jan 2014) but, even in those far off times, it wouldn’t have been enough to build the mansion house in Leith and pay off the Logan debts.
 It is also unlikely that a small-holder at Lochend would have accumulated enough of the  penny siller  to make George Logan throw his hat into the ring with the other suitors.

Ten cam' east and ten cam' west and ten cam' sailin' ower the water
Twa cam' doon yon lang dyke side, there's ower mony wooin' at her

 No, for my money, and for Tibbies’, it has to be Isabella Fowler of Burncastle.