How many short rests can you take per day?

Question

Is there a specific rule that limit the number of short rests per day like the one that say that a character can't benefit from more than one long rest in a 24-hour period?
My friend is playing a sorcerer-warlock multi-class and sometimes when the party is waiting or walking in the city buying things or traveling in carriage he:

• converts sorcery points in extra spell slots

• converts the warlock spell slots in sorcery points to regain the sorcery points he just used

• take a short rest to regain the warlock spell slots

In this way he usually has more than the normal max spell slots until he makes a long rest, generally lvl 1 spellslots to cast Shield in most of the fights to boost his AC and avoid damage.

Answer 1

There isn't a hard and fast rule

While the general design model fits two short rests into each adventuring day, it can be fewer or more depending upon the pace of play.

After a short rest, the DM decides how much time must elapse or how much activity must occur before another short rest can start. Maybe 0 minutes, 1 minute, 10 minutes, or 1 hour. The key is that rests aren't meant to be a button you press. They're a narrative pause.

That's from the thinking by one of the game's devs(Jeremy Crawford). If a player declares to you "I am taking a short rest" you are not required to grant it. As a DM (and as a group) you need to figure out "does it make sense to do this narratively?" before you deal with the mechanics of the short rest.

Insofar as what the rules say:

Short Rests
In general, over the course of a full adventuring day, the party will likely need to take two short rests, about one-third and two-thirds of the way through the day. (Basic Rules, p. 166)

If you are the DM, the benefits of a short rest come when you say they do. (DMG p. 5, Master of Rules). I'd recommend that you read up on the DMG section that covers the adventure day to get a feel for what is behind the point of long versus short rests.

What is resting, anyway?

From the Basic Rules, p. 70

Resting

Adventurers, as well as other creatures, can take short rests in the midst of a day and a long rest to end it. {snip}

Short Rest

A short rest is a period of downtime, at least 1 hour long, during which a character does nothing more strenuous than eating, drinking, reading, and tending to wounds.

No mention of walking there.

A character can spend one or more Hit Dice at the end of a short rest, up to the character’s maximum number of Hit Dice, which is equal to the character’s level. {snip}

A short rest can also be 3 hours long, for example.

Long Rest

A long rest is a period of extended downtime, at least 8 hours long, during which a character sleeps or performs light activity: reading, talking, eating, or standing watch for no more than 2 hours. If the rest is interrupted by a period of strenuous activity—at least 1 hour of walking, fighting, casting spells, or similar adventuring activity— the characters must begin the rest again to gain any benefit from it.

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A recent update to the Sage Advice Compendium supports this answer:

Adventuring
[NEW] Is there a hard limit on how many short rests characters can take in a day, or is this purely up to the DM to decide? The only hard limit on the number of short rests you can take is the number of hours in a day. In practice, you’re also limited by time pressures in the story and foes interrupting.

Answer 2

First off, the need to understand the class abilities / mechanics:

Sorcerer

• Spell Slots - regain after long rest! (PHB pg. 101)
• Sorcery Points - regain after long rest! (PHB pg. 101)
• Flexible Casting - conversions are bonus action (PHB pg. 101)
• Sorcerous Restoration - level 20, gain 4 points after short rest. (PHB pg. 102)

Warlock

• Spell Slots - regain after short or long rest.

Multiclass

• Pact Magic - ... use spell slots you gain from PM feature to cast spells you know or prepared from classes with Spellcasting class (PHB pg. 164) feature and vice versa.

So there is a breakdown of actually using the mechanics correctly.

1. Sorcerer regains slots and points only after LONG REST
2. Flexible Casting isn't compatible with Pact Magic (JC tweet contradiction, Intent vs Written)

Walking isn’t resting. Walking for 3 hours definitely doesn’t constitute as resting. Rest by definition is inactivity, especially motionless. Hence eating, drinking, reading...

All this needs to be addressed with the DM.

The whole point of short rests is to recoup a bit of the party's combat capacity at the cost of a minimum of one hour's inactivity. The intent of this is to reduce the dependency of magical healing and giving "some" spellcaster extra low level juice throughout the day.

There maybe no limit to short rests, but claiming to rest after every battle breaks narrative gameplay.

I standby that Pact Magic isn’t compatible with Sorcery point conversions as written

Written > Intent