1) Could mean 'against' as in, 'side by side with' or 'next to' but in the sixteenth century was used in the sense of 'towards' or 'with regards to'.
The etymology of ‘anent’ is interesting, for it is said to derive from the Old English on efen, or on even if we use the modern equivalent: 1420 the post ... anent the lede in the same workhouse, York. It can be compared with ‘again, against’ and meant literally ‘on a level with’ or ‘side by side with’: it progressed to ‘anent’ and ‘anenst’ via Middle English onevent and the former spelling survived in local dialects: 1782 a man pulling a Piece at Lowwestwood Mill anent another man, the hands slipping, fell backwards into the millrace, Golcar. It could denote position, with the meanings ‘against’ or ‘next to’, as in a Wakefield by-law of 1556 which required every tenant to make the pavement anenste his house . In a South Crosland title deed of 1570, a riverside meadow was said to abut upon the landes of Richard Beaumont, esquire, anenste the weste … and upon the water of Colne anenste the este . Similarly, in 1584, the manorial boundary in Almondbury was said to run along the bottom of the Netherwooding, right anenst the north side of … Robert Royd Ing. In many sixteenth-century examples ‘anenst’ meant ‘against’ in the sense of ‘towards’ or ‘with regard to’, and this occurs in a document of 1443 which referred to riotous behaviour at Fountains Abbey. Those involved, including Sir John Neville, were ordered to kepe the pees anenst th’abbot and convent … and their servantz and welwillers. The word also occurred quite frequently in situations where an individual sought to discharge himself of some liability. Typical expressions in this case are: 1481 theise oure lettres shalbe your sufficiant warant and discharge anempst us, York
1552 so that he shall discharge me eneynst the Kynge for my haryotte. The ‘haryotte’
that is heriot, was a feudal payment made by an incoming tenant - often his best beast. Also at Fountains there were penalties in 1520 for trespasses doon … both anenste dere and woddes. Unusual spellings are commonplace: in a York document of 1590 it was agreed that whoever should laye anye dounge in Hungate enenpste the Frear walles should pay for every burden 12d.