If you share your area, im sure you could get more info/help from those that live nearby...maybe even some sales offers.

There are a lot of questions here that have more than one answer and on a sliding scale.There are also answers to all of them on this site.

Are you looking for a specific game (s)? Do you have a list?

Buying remotely:

I recommend you don't...at least, not for your first pin. There are pins everywhere. If you are willing to pick up within a few hours drive, you would likely be amazed at whats out there. Shipping usually costs around 300-600 in the contiguous U.S. and goes up from there. I like to use Michelle at STI or Dan Scott.

Game selection:

Nostalgia is a major factor for many. I would certainly suggest playing as many pins as you can and/or watching as many videos of people playing them. These can be found on pinside under the gane listings in the top 100 or also on youtube. You seem to have an idea on era, but you could really nail down a favorite this way.
I also suggest being open to any title that comes up and give it a little research. I have cone across many unexpectedly nice pins that i wouldn't have originally considered by doing this.

Appraisal:

Pinside is great for this, but it isnt always 100% accurate. Make sure to check recent sales and factor in condition. You can also look at ebay historical listings and check out other pricing guides online.

Key things to look for in photos:

Obvious wear and tear...especially to the playfield. If you have any repair skills, this can certainly make a difference in what is more important to you or not. How dirty is it? Are there worn rubbers and lights out? Is the backglass flaking? How are the boards? Is there any acid on the mpu? Are there any burn marks on connectors, coils, etc? How hard are parts to come by if something if missing/broken?

Fair counters for issues:

Once you see a pin you like and look through it, make note of anything and ask about it. Sometimes pics dont tell the whole story and even in person there may be a spare or a quick fix available. Otherwise, i calculate the cost of the issue (part(s), my time, difficulty of obtaining parts, and my skill level to do any upgrades/repairs) and subtract that from the price. This is all very personal to you and your resources. I recommend you buy something in the best shape you can as your first pin...and if you want to tinker...a project for your second pin.

Cabinet fade:

This depends on how bad it is and how much you care about it. I sold a very nice and desirable game a couple years ago to free up some cash. I sold it cheap. Too cheap. The first guy to look at it passed because it had slight cab paint chipping (easily fixable....but it was really hardly even noticable). The second guy couldnt get his money out fast enough. He almost burnt his hand going for his wallet so fast. I had a line of 4 others buyers contacting about it all behind the line that were ALL offering me above ny asking. The moral is that sone people dont care about cabs much and for some it is a deal breaker.

If you have a big issue with the cab, voice your concern and see if the seller would come down. If it has to be re-done completely, i would take off 400...but this is really subjective.

LEDs:

Very subjective. Some people subtract value from a game having LEDs. I have tons on hand, so it's not a big deal to me. If you love LEDs and desperately want them...you can add 100-200 in price.

Shipping and payment:

Once again, i highly recommend you DON'T do this for your first pin. Go see it in person. Keep looking on those sites and pinside. Make friends with local collectors. Use the pinside map and contact some people local to you. Place a wanted ad on here. Look on regional threads here on pinside. Share what area you are in on here and ask if anyone knows someone local to you. There are tons of options.

For the payment, always use cash. If you have to use something else because you have to ship, check out this thread:
https://pinside.com/pinball/forum/topic/attention-don-t-get-scammed

These are the only shippers i trust:

Michelle Bianchi
800-959-8880
cell: 630-344-3093 [email protected]

Dan Scott
864-903-1324