as others have posted.
finding a V8 car for $5K will be difficult. if you do find one it will probably be a fixer upper type car unless you get lucky.

i will add to the suggestion list.
C4 corvettes. these cars are somewhat difficult to work on so they are the cheapest of all corvettes. they have significant online support and best part of them is parts are usually not that difficult to find and reasonably priced. there will be some $$$ and difficult to find.
Fox body Lincoln Mark VII, T-Birds and Fairmont's.. these cars use the same drivetrain as a Fox body mustang. there is significant online support so working on them isn't hard and most parts are reasonably priced. And not difficult to find. some parts especially the Lincoln's will be really hard to find.
Lincoln mark VIII. they have the same drivetrain, 32 valve V8, as a cobra mustang. they have .so so online support. bad part is they are a pain to work on. breakdowns are common. parts are somewhat difficult to find and are $$$. these cars can usually be found pretty cheap for these reason. NICE cars can easily be found in the $5K range.

a non V8 car to look at in his price range that might tickle his fancy. S197 V6 mustangs. 05-09 cars needing work can easily be found in the $5K range. he might even find a V8 car needing work in his budget. from the outside no one will know it has a v6. significant online support. for the most part easy to work on and reasonably priced and easy to find parts.

i myself have a supercharges 08 Bullitt mustang. it's faster than 80% of the cars on the road. drives and rides great. is actually rarer than most mopars and the best part is i have less in the car than it cost to build a hemi motor that was in my 72 Roadrunner.

Prices are high but ..

I had a really nice 1 owner , 79 Aspen two door , tried to get $3500 for it for over a year , gave up sold it cheap to a friend

Well said! I sold my car for half what some people (and ‘dealers’) are asking, but I got what I would have thought was a fair deal if I was buying. There are some pretty nice cars near me that have been for sale for over a year…the sellers are asking top dollar and are willing to wait for that motivated buyer. I do think the muscle car market is higher than it should be for the regular cars…a ‘69 318 Coronet 440 isn’t worth $20k (to me) unless it’s in perfect condition - not something with rust around the rear window and a tired interior.

Buyers: "Prices for junky cars are ridiculously high and the sellers won't come down!"
Sellers: "My car is priced for half of what I put into it and just a bunch of tire kickers calling but not making a serious offer!"

A tale as old as time--it's all about your perspective. (The truth is actually somewhere in between.)

Something that might help the guy out - assuming he has more money to spend without messing up family life - is to get something that will hold or increase in value.
Obviously, that can move the purchase from scratching an itch into investment territory.
I'm interpreting the guy's desire as being a vintage ('60s - '70s) car, though some '80s cars are appreciating.
Of course, a lot depends on his ability and/or desire to repair/spiff up a vehicle, and whether he wants/needs a turn-key deal or has the time, patience, & funds for a project.

IMOP a IF you find a $5K V8 classic type car. it will probably need a fair amount of work to get it on the road. you will probably probably have about $8-$10K in it to be a decent driver.
as posted earlier spend a little more for a nicer car and in the end it will actually be cheaper than the budget car.

honestly if things were a little different for me financially and i have the space i would be all over this $9K 08 Bullitt mustang that looks to be a turn key driver..
in spring time this would be a easy $12K -$15K car. i am surprised a flipper hasn't picked it up already. he lists it as having 555,000 miles but the odometer reads 55,000.miles. he thought the tenths were actual miles.

https://winstonsalem.craigslist.org/cto/d/lewisville-08-ford-mustang-bullitt/7808493649.html
.

Wow! That's a nice piece for that price! I have the 9k but not the time to fetch or place to put it. Site prep on my new small toy barn was done today but the building won't be done till spring. Timing is everything and mine always sucks....lol

I like that mustang too! This seems like a good deal…sale price seems reasonable.
68 GTX

At that price point it isn't something you'll find online...

That is something someone had tucked away and just wants to sell...

It may be something coming out of an estate sale...

It isn't going to be just waiting for someone to come take it...

He'll have to be the first to find it and have the money in hand...

I always take my trailer if I hear of a good lead on something...

that ad was written by an idiot. I'll pass on dealing with an idiot's leftovers.

Is he open to a truck? I talked to a guy with some big block dodges this fall. Would be around his range and be fun.

That's kind of how I got my Imperial last fall.

A friend of mine at a cruise nite told me about it and that he was thinking of buying it. He passed but not because there was anything wrong with it and called me.

It was in the OP's price point, that is to say a you can't not buy it price.

47k original miles, unmolested. Still had L78s on it.

Kevin

That was good timing seeing as how you only get about 6 weeks of good enough weather for cruises...

Too many guys get hung up on having to have rare...matching numbers stuff...

Mine are all Mutts and I have a blast in all of them...

Kevin I did take the Duster to the track in November...11.93 @ 112 mph with 3.55 gears...

That car was a good find when I bought it in 2016 and would have fit into the ops budget...

The only cars you might get for $5000 that are worth buying are probably old luxury cars. Everything else will probably be a project of some sort. You can find some decent trucks for that. A rust free 1st Generation S10 with a V8 isn't hard to find and can be bought for $5000.

i don't think common S10's came with a V8. except for the limited edition, and expensive, Cyclone or Typhoon or something similar to that name.

No factory V8 S-10s. The typhoon/cyclone was a turbo V6.

Iron duke S-10's are really cool, if you can find a rust free example..it won't be fast, but it's gonna get you to your destination.

Does your friend have any experience with an "old" car?

If he's expecting a get in, turn the key and drive experience for $5k, he'll be disappointed unless he finds a screaming deal.

Not trying to be a Karen about it but his budget is only going to get him a car that's going to need more work to be dependable.

True. Even the Typhoon and Syclone were Turbo V6s. I thought I might have mentioned V8 swap, but I didn't. V8 swaps, especially the GM small block (327, 350, 400) are fairly easy in them and fairly easy to find already done.