The earliest 2.3-16s you'll likely find will be '86/C, although there were a tiny number produced on 'B' plates over here. Quite long order times for these cars it seemed, on my old 2.3-16 that was registered in January 1987, the original order sheet was from late 1985.
As Neil says, automatic transmission was an option for the 2.3-16, although the especially revvy/peaky nature of the 2.3 engine made for a less suitable match than the later 2.5-16, and hence the 2.3-16 Auto is a rare car - perhaps a special order even, but I have certainly seen a handful
Many 2.3-16s suffered chain issues over the years, I can recall several cars and people who have had such problems. The main issue was the tensioner design - MB later improved the tensioner to reduce the amount of slack on the chain upon start up (they have a one-way ratcheting design to maintain tension at rest). If the chain has been running worn for any length of time, chances are that the sprockets and guides will be knackered - you're looking at well over £1k in parts alone, and the entire timing case will need to be removed to gain access - not a pleasant job and ££££s of work at a specialist. Several people have replaced the simplex chain and sprockets for the stronger and more reliable duplex chain system at this stage - you wouldn't want to do that job twice.
A good many cars have been written off due to simplex chains snapping, the damage caused by such an incident can lead to a bill of several thousand ££££s - very important to check for wear and be aware of any unusual noises. IMHO, in view of the relatively low cost, I'd replace the simplex chain at around 60-100k miles, and definately replace the tensioner if of the earlier design.
Generally, I'd say you've got more chance in finding a well maintained and non-rusty 2.5 over a 2.3, due to age if nothing else! The later 2.5 cars have a bit more power and noticably better midrange, although the character of the earlier 2.3 is perhaps a little more 'raw'. 2.5-16 also gets slightly more standard equipment (ASD, rear headrests) as well as two other colour options - Almandine red and Astral silver.
At the end of the day though, these are all old cars now - anything from ~ 17-25+ years old. Originality, body condition and documentation/history would be more important than age/mileage itself. Most of these cars have suffered from abuse and poor maintenance by now, so you're in for a battle if you're keen to hunt a good one down. After my first 2.3-16 that I sold on, it took me nearly two years to find a suitable replacement
Great cars though - miss mine immensely at times, a fanstastic driving package with plenty of classic appeal in the making
IMHO, it's worth paying a lot more for a good one, if you can. £5-10k+ is where the really nice cars are, full MBSH/specialist history, lower miles, 3/4 owners etc - a better long term bet than a cheaper car which invariably will cost a lot more to run during your ownership. Parts and maintenance for these cars wasn't cheap 5-10 years ago - now they're getting on a bit, spares are getting harder to find and the typical cars are more tired/tatty - hence you can spend ££££s on bringing an average example up to scratch.
Been there, got the T-shirts
All IMHO and experience of course, and not intended to upset anyone
Will