I live in Maidstone and have done for the last 8 years or so and before that lived in a village not far from it called Staplehurst - so basically Maidstone is my home town.
My thoughts on it as a town...
Shopping is pretty good as far as high streets go and has al your typical shops. It hadn't been hit much by the economic down turn since 2008 but over the last year or so it seems to have suffered a bit a some shops have gone but if you're a fairly standard sort of person you'll find what you're looking for.
Eating out is great, there is pretty much everything you could wish for from a decent greasy spoon up to some lovely restaurants. You'll find pretty much all the main chains here including Nandos, Pizza Express, Zizzi, Prezzo etc. Most of these are situated on one street which is becoming a nice eating area. In addition in the surrounding area there are some lovely pubs that do amazing food and some truely fantastic restaurants about.
As for parking, there is actually masses of parking it's just that some of it is spreadout and hidden away a bit bit if you get to know the area you can always find a space!!!
Dodgy Areas...
As with pretty much any town there are some dodgy areas some are complete no go zones others you just need to avoid certain parts.
For example: Tovil
Avoid Coombe Road and Courtney Road as they are truely hideous however not far away at Tovil Green (literally half a mile away) there is a lovely set of estates which are really peaceful and quiet and some really nice houses.
My Rough off the top of my head guide to areas of Maidstone
1) Senacre - largely ok, a few areas to avoid.
2) Shepway - Largely avoid though there are some nice roads tucked away (I live on one such road)
3) Park Wood - Avoid
4) Mangravet - avoid at all costs!
5) Tovil - Some nice areas but some very rough areas too
6) Downswood -largely speaking ok
7) Bearsted - Nice
8) Weavering - Nice
9) Boxley - Ok though some areas to be avoided
10) Otham - nice
11) Sandling - nice
12) Ringlestone - avoid
13) Larkfield - ok
14) Ditton - nice
15) Detling - Nice
16) Barming - Nice for the most part
In the surrounding area there are some really really nice villages which are close enough to make Maidstone very handy but far enough away to be nicely rural, and a lot of them are on the trainline to London.
examples on train line:
Hollingbourne, Harrietsham, Lensham,
Examples not on train line:
Leeds, coxheath, Boughton Monchelsea, Linton, Langley
A bit further out you also have some nice villages which are on a different fast commuter line:
eg Marden, Staplehurst, Headcorn.
hope this is of some help.