I know the town well from passing through it and stopping the odd time (not from a schools perspective though) and it is a really decent place that has come along loads in the last few years. Leitrim gets alot of bad press for whatever reason but this town is a hiden gem with all the major shops Lidl, Tesco etc and a gorgeous place to spend an afternoon. If I personally had an opportunity to live there I'd jump at it.
If you plan on buying a home I would avoid many of the newer estates in the town as few of these are not owner occupied. There isnt any anti-social behaviour in these developments, Its just that some of the houses in them are getting a bit grubby.
If you have a young family have you considered looking at some of the surrounding villages.
Leitrim Village and Jamestown/Drumsna are both nice riverside villages and seem to be popular with owner occupiers.
I havent lived in the region in a couple of years but I recall at Primary level the Gaelscoil had a good reputation. There was only 1 secondary school (Community School) which had a good reputation.
The town centre has good pubs and restaurants and the town gets busy at Saturday nights. The arts centre used to get decent music and comedy acts.
Shopping was continuously improving but I found that the nearest big shopping town was Sligo (40 mins away)