Anyone currently training (or have in the past) for an amateur fight?  I'm looking at getting into the sport.  Advice/thoughts/stories?

There's a lot to training for amateur MMA, it's hard to condense it down to a post reply.
I help coach our amateur fighters and here's our basic gameplan for their first fight:

Get yourself a great cardio base.

Work with a boxing coach on an easy combination. "Jab/Jab/Right Cross/Left Hook" is Boxing 101 and you should have this down pat.

Work with some college wrestlers on shooting a single leg takedown and sprawls.

Work with a Judo or BJJ coach on a head and arm hip toss from the clinch.

Work with a BJJ coach on surviving/escaping the mount, taking the back with hooks and wrist control, rear naked choke both attack and defense.

Having a solid understanding of simple striking, a couple of takedowns and some simple ground survival skills as well as a high percentage submission will take you a long ways in your first fight.
Almost every single first fight our guys have had for years ended in either a decision, TKO from strikes (usually the ref calls it for a cut of lack of active defense) or a rear naked choke.

Also get used to claustrophobic pressure, both in your standup and on the ground. We always have our fighters spar/roll with our extreme pressure fighters.
Even guys with great cardio gas out quick unless they're somewhat inoculated against pressure/stress.

When two first timers are going at it:
Both are gassed out halfway through the first round from holding their breath due to excitement/stress.
Rarely do kicks play a factor.
Rarely does the ground game get technical.
What you usually see is a few strikes followed by a lot of clinching up and attempts to bulldog each other to the ground.
Once on the ground it'll either be a TKO once the guy starts ground and pound from the mount or the RNC when they flip over to get away from getting punched in the face.

Bro, how long have you been training?

I've been a martial artist for 35 years, this September 2nd. And I had my first MMA fight in 1993. It was eye opening to say the least.

Back then, the guys that fought had years and years of experience. Nowadays, guys with only a year or two of training are getting into MMA. And while it may be satisfying to get in there and fight; you are risking doing a LOT of damage to your body.

Could you effectively lay out a strategy for your grappling game? Meaning, what you'll do for guard retention, takedowns, top game, side game? Do yo have a striking strategy?

Why not consider grappling tournaments to see where you stand? And doing some amatuer Muay Thai, to see where your striking stands?

I teach now, and do grappling competitions, a LOT. And if I got a dollar for every time someone came in off the street, and said that they wanted to fight MMA, I'd have one helluva personal armory. Most guys think that they can fight; they think, how hard could it be? Then they get reality.

I'm not saying to not go for it, just be aware of what you're getting yourself into. Make sure that your medical insurance is excellent. You're going to get as many, if not more injuries in training, than you will from a fight. And you will then earn some nagging injuries. Make sure that this is worth it to you.

Bro, how long have you been training?

Could you effectively lay out a strategy for your grappling game? Meaning, what you'll do for guard retention, takedowns, top game, side game? Do yo have a striking strategy?

Why not consider grappling tournaments to see where you stand? And doing some amatuer Muay Thai, to see where your striking stands?

I've been training for about 5 years total (24 years old).  I have 4 years in Kajukenbo under a very experienced MMA/kickboxing guy, 1 year in BJJ, a few months of boxing, a month of Kali and, a few other assorted classes.  Lots of cardio/endurance focused workouts.

My grappling game:  sounds cliche, but: position before submission, use strikes to setup technical movement and submissions, keep good defensive posture above all.

Takedowns:  double leg, single leg, a few judo hip throws, pull guard w/guillotine choke
Guard retention:   DON'T GET ROCKED BY PUNCHES, control head/biceps, over/underhooks, reguard, use butterfly guard, setup sweeps by striking, use open guard to setup technical standup or maintain distance.  Guillotine, Triangle, arm triangle chokes if available.  Working on some spider guard applications.

Side game:  pass to mount, attack ribs w/knees&elbows, americana, take back when possible

Top game:  take back, strike to create openings.  Avoid subs that potentially sacrifice dominant position.  Get good hooks ASAP

Striking game:  Leg kicks, work off-angle attacks, counter punching, lots of body shots from inside, knees and elbows in clinch, setup takedowns.  Push the fight tempo

Sorry for the long-winded post.  It's a difficult subject to condense (obviously).

I live in a small town about 2.5 hours from anywhere with significant training opportunities.  I've done well sparring with other guys that are succesfully competing in amateur Muay Thai.  There are no grappling tournament opportunities within several hours, but I would absolutely love to get into a few.

Most critical thing of all?
Have a coach who knows how to work with the promotor to match up fighters.
Our head coach does an amazing job of making sure our fighters are evenly matched up with their opponents.
I see a lot of very lopsided fights setup by inexperienced coaches and shark promotors.
You have to have a coach who's looking out for you and won't let you walk into a no-win fight just to pad the other guys record.
Two evenly matched amateurs makes for a fairly safe fight (no matter their skill level) as long as the ref is good.
A lopsided fight is where the less skilled fighter gets hurt.