1) THE LIABILITY OF THE BORROWER FOR AN ITEM IN TRANSIT
OPINIONS: The Mishnah (98b) teaches that when a lender sends his item to the borrower via a servant, the responsibility of the item en route depends on whether or not the borrower asked him to send it in this manner. If the borrower asked the lender to send it with a servant, the borrower is responsible for the item once it is given to the servant. If the lender decided on his own to send it to the borrower in this manner, the lender is responsible for the item until the borrower receives it.
The Gemara asks, why should the borrower be responsible for the item right away when he asks the lender to send it with his servant? There is a principle in Halachah that the hand of a servant is considered the hand of his master. Accordingly, as long as the item is in the hand of the servant, it has not yet left the lender's domain. Why, then, is the borrower responsible for it?
Shmuel answers that the Gemara refers to a case in which the lender sent the item with his Eved Ivri, not with his Eved Kena'ani. An Eved Ivri is not the possession of his master, and therefore his hand is not considered like that of his master. Rav answers that the Gemara may even refer to a case in which the lender sent the item with his Eved Kena'ani. The reason why the borrower is responsible is that it is as if he told the lender, "Hit it with a stick and it will come."
What does Rav mean? The borrower never took possession of the animal, and it is still in the hands of the Eved Kena'ani. Why should the borrower be responsible?
(a) The RITVA quotes some who explain that it is as if the borrower said to the lender that he should lead the animal to a side street, or to the sides of Reshus ha'Rabim, so that the borrower can acquire it there through Meshichah (unlike Reshus ha'Rabim where he cannot acquire through Meshichah). However, the Ritva says that he does not understand this explanation. Meshichah was not actually done by the borrower, and thus he never took possession of the borrowed item.
The explanation which the Ritva cites is the opinion of TOSFOS (DH Keivan). Tosfos explains that it is considered as though Meshichah was done when the animal is brought to a side street or to the sides of Reshus ha'Rabim with the express intent of the borrower to acquire the animal through this act (of leading the animal into the side street). Alternatively, Tosfos explains, it is possible that even if the animal was led to Reshus ha'Rabim by the slave due to the explicit request of the borrower, it is enough to make the borrower responsible for the animal (even though Meshichah normally is not a fully effective Kinyan in Reshus ha'Rabim).
(b) RASHI (DH Na'aseh) explains that the reason why the borrower is responsible is not due to his status as a Sho'el. Rather, he is responsible because he asked his friend to send the item with his servant, and by making such a request he effectively accepted responsibility for the item. Just as a person can tell the owner of an item to put the item somewhere and he will take full responsibility for the item even without making a formal Kinyan to that effect, a borrower can tell a lender to send the animal with his servant, and it is tantamount to saying to the lender that he should let the animal find its way and he accepts full responsibility for it. Although, in this case, the borrower does not say explicitly that he accepts full responsibility, Rav explains that it is considered as though he said so. (Y. Montrose)

99b----------------------------------------99b

2) WHAT FORM OF "KINYAN" IS VALID FOR "SECHIRUS"
OPINIONS: The Beraisa states that just as Meshichah was established as a Kinyan for buying, it was also established as a Kinyan for Shomrim. Moreover, just as land is acquired through the Kinyanim of Kesef, Shtar, and Chazakah, the obligation of Shemirah may be acquired in these manners as well. The Gemara then asks about what type of Sechirus was done. What is the Gemara's question?
(a) RASHI (DH Mai Avidtei) explains that the Gemara's question is how can the Beraisa say that a Shomer can acquire an item through Chazakah without the process of Meshichah? Chazakah on a movable item means that the Shomer performs Meshichah! The Gemara answers that the Beraisa refers to someone who must guard land.
The RITVA asks that this does not seem to be the Gemara's question. If the Gemara assumes that the Beraisa refers to movable items as well, it should understand that when the Beraisa says "Chazakah" it means "Meshichah"!
(b) The RAN understands Rashi differently. He understands that Rashi maintains that the Gemara's question involves the Kinyan of Kesef. Just as movable items are not acquired through a Kinyan Kesef (because of a Gezeirah that after the buyer gives money to the seller, the seller will not bother to protect the merchandise from destruction; see 47b), the Sechirus of movable items is not "acquired" through Kesef. Hence, the Beraisa must not be talking about the Sechirus of movable items when it mentions the Kinyan of Kesef.
The Ran questions this explanation. He asks that there are cases in which money is considered a valid Kinyan for movable items, and thus the Gemara would not ask such a question. He then gives the same explanation as the Ritva (see (b) below).
There seems to be a third difficulty with Rashi's explanation. RAV YOSEF SHALOM ELYASHIV shlit'a (quoted in He'oros b'Maseches Bava Metzia) points out that the Gemara in Bava Kama explicitly explains the question. The Gemara there asks, what kind of Sechirus is the Beraisa discussing? The Beraisa cannot be discussing movable items, since movable items cannot be acquired through the Kinyan of Shtar. The Gemara there answers that the Beraisa must be talking about land. Why does Rashi here veer from the way the question is explained by the Gemara itself in Bava Kama?
(b) The Ritva explains, therefore, that the Gemara is asking about the Kinyan of Shtar. The Gemara's question is based on the Gemara in Bava Kama (79a) which teaches that the Kinyan of Shtar does not apply to movable items. Why does the Beraisa say that they are acquired through Shtar? The Gemara answers that the Beraisa does not refer to movable items, but rather to land. (Y. Montrose)