We're just now going to go into 5th edition. A player has expressed missing 3.5 which we played for years. Since there is no online support at WOTC for 5e we're planning a character generation night with one encounter which I play tested successfully with my kids. Still, I'm facing the desire of a regular to try 3.5 again. How have players of older editions found 5e in comparison? Positive? Better Worse, broken? Too Restrictive?
Simply put: 5e is very much like 3.5e, except where it's not.
Expanding: I don't mean that facetiously. The two are like siblings with very strong family resemblance and a small age difference--not twins, but if you casually pass one in the cafeteria, you might mistake one for the other. But in the handful of places where they're different, it's a pretty distinct difference.
To my mind, there are four really big differences between the two.
1. Casters are reduced in power, and (primarily) non-casters are increased in power.
This is not to say that I think they actually eliminated or "solved" the LFQW problem; I think it's still present in 5e. It's just not
nearly as dramatic; casters have some specific and important limitations, and non-casters have been brought up a notch. (If you're familiar with the "tiers" classification from 3.5e discussions, I'd argue that 5e forces all classes into the equivalent of tiers 2, 3, and 4--still a noticeable gap, but not so great that you're playing Casters & Caddies by 10th level).
2. Magic items are
dramatically de-emphasized.
The designers said they were designing assuming no magic items, and they meant it. Giving them out at all like you're used to in 3e will take the already-unsteady encounter difficulty math and crush it. Further, no "standard" magic item goes above a +3 AFAIK; many items (some powerful, some...less so) require Attunement and you can only Attune three items total; and there are essentially no 'price' guidelines for the vast majority of items (the provided rarity/value comparison is
hella wonky).
3. Combat is mobile and "theater of the mind."
Like 3e, you provoke opportunity attacks if you try to leave an enemy's range. However,
unlike 3e, you can split up your move before and after you attack--for classes that get Extra Attack, you can blend movements and attacks as much as you like. Also, although there's still just as much of the stuff that made third edition battlemap-centric (everything is listed in five-foot increments, many spells are more natural snapped-to-grid), the game takes pains to make "theater of the mind" (gridless, abstract-position) combat core. So things are much "looser," combat-wise, than in previous editions.
4. Customization and character-building are dramatically reduced.
3e became almost notorious for the level of intricacy you could get into, with LAs, ACFs, substitution levels, PrCs, skill points, and feats--and that's not even counting the really out-there stuff like flaws, traits, etc. 5e admits almost none of that. Feats are chunky but extremely limited--even the Fighter, that gets extra, only gets 7 over the course of 20 levels (compared to the 18 a 3.5e Fighter got)--and they compete with stat-boosting. Backgrounds allow a lot of 'flavor' customization, but very little advancement. All classes get subclasses, which sometimes take the place of PrCs or other feature-alterations, but you lock those in
very early and cannot change them later. There are no skill points, only Proficiency, and RAW you can't gain new skill proficiencies after chargen (tool proficiencies can be, though). On the whole, it means that several
complete builds are core-supported in 5e, but comparatively none of the "build your character from 1 to 20, your way" stuff remains.
If your friend is a fan of uber-powerful casters, high-magic/many magic items, low-mobility/precise combat, or deep customization options with many choices to make, 5e will probably not please them.
If your friend prefers to play non-casters (or "secondary" casters, like the Paladin), likes magic items to "feel magic," likes mobile/"theater of the mind" combat, or hated the character-building minigame, 5e will probably feel like the second coming of 3.5e.
Though I strongly recommend, if your friends are all experienced gamers, that you start no lower than level 3. Level 1--from personal experience, now--is
extremely fragile, and gives you few if any resources to work with. Also, some subclasses (like Valor Bard) don't kick in until level 2 or 3, which can seriously hamper players shooting for a particular archetype.
Oh, there's one last change, though AFAICT everyone who hears about it sees it as a straight-up improvement. "Finesse" is no longer a thing you have to invest in. Anyone can fight using Dexterity as their main offensive stat, they just have to use a weapon that has the "Finesse" tag, such as the rapier (1d8 damage, as good as a longsword) or scimitar (1d6). This does, however, have the consequence of making Dexterity an extremely attractive stat for many characters, as it then determines AC, the most common spell save, attack, damage,
and Initiative--plus helping all the old Dex skills like Stealth. No other stat can claim such broad appeal, but the general consensus (which even I share) is that that's better than punishing people who want to play a Dextrous Paladin or Fighter.