"Rabban Gamliel said, make for yourself a rabbi, remove yourself from doubt, and do not frequently give tithes by estimation."
This is quite a difficult mishna and the difficulty is in its last statement.
First, it is pretty clear that Rabbon Gamliel is driving at encouraging exactness. He says that one should have a Rav, presummably to teach and to answer questions and that one should avoid doing things out of doubt. The third statement appears to go in the same direction. We can see that it advises us not to give tithes (maasros) by estimation and that we should be exact when we give tithes. The difficulty with it is technical. It appears to imply that what is wrong with estimating tithes is that one whould not do so frequently or that it is not a laudable type of behavior. In fact, however, tithes are not valid to any degree, small or large, if given by estimation. Maasser must be given as one out of a hundred. If one gives less, not all of the chullin is "fixed". If one gives more, the maaser contains chullin, instead of all being maaser.
The mishna may be making a larger point but it appears to be wrong on a basic fact of halacha, which is expressed in the mishna 6 of the fourth chapter of Terumos. According to most commentators it is speaking of maaser and terumas maaser. These have to be measured exactly, one part out of a ten. Even if we explain the mishna to refer to teruma instead of maaser, the general principle that maaser cannot be given by estimation is well established and is so codified by Rambam. What happens if one takes maaser by estimation is that either the masser which is taken or what remains consist of a mixture of maaser and chullin and this creates significant halachic problems. (See Bartenura here in Avos). Instead, what should be done is that a basket is measured so that exact tenths can be separated.
In three periods of they year a basket is measured: When the first fruits come in, when the last are harvested and in the middle of the gathering process (Terumos 4:6).
So what does one do with a halachically inaccurate mishna?
Maharal in his commentary suggets that this mishna expresses the view of Abba Elazar ben Gomel in Eiruvin 50a, who holds that maaser can be taken by estimation in the same way that teruma is taken by estimation (this is the case biblically, rabinnically teruma also has a minimal shiur of 1/50, 1/40/ or 1/60). If this is so, we have a stam mishna agains halacha and also against another stam mishna in Terumos 4:5, which says, "He who counts (out the exact amount of maaser) is prasieworthy and who he mesures is more praiseworthy than he, and he who weighs is (even) more praiseworthy than he.
Ein Lavanon attempts to prove that one is not allowed to ad initio take more than a tenth or less than a tenth. However, if he estimates a tenth, even if he miscalculates, the result is not considered a mixture of maaser and chullin. This is a novel approach and not shared by others.
Jewish ingenuity being what it is, one can always find an exception to the rule of maaser needing to be taken exactly as one tenth. If one can find such an axception, he can then explain this mishna as referring to such an exception. Tiferes Yisroel objects to any attempt to see this mishna passage in purely technical terms of the laws of maaser becasue Avos is not a place in which maaser should be discussed. I'd add that it is also not a place in which exceptional and unusual halachic cases are displayed. Instead it is a tractate that teaches good character and moral living. It is not a showcase for presenting halchic curiosities. It is certainly not an opportunity to display halachic vitruosity.
Tiferes Yisroel is certainly correct on this. However, there may be a place for a particular type of exception even in a tractate devoted to middos. If you find a maaser law that is very common, a part of daily life and that everyone encounters, it can serve as an example of a midda or behavior. This is the kind of an example that I propose to explain this mishna.
Imagine that you have a whole storehouse of grain that you just harvested. Common situation, no? A Levite or a poor person come to visit you. This presents a difficulty, for you have nothing to give them except what's in the storehouse, but you cannot give them from the storehouse there because it has not been tithed. Of course, you can take out some grain and tithe it and give the maaaser to the Levite/poor man and keep the chullin for ourself. You will then have to find a place to store this chullin that already has been fixed but you can't jsut throw it into in the storehouse, where the produce that is still subject to maaser is being stored. Or, you can give them their maaser portion, and leave the now fixed chullin in the storehouse together with the reminder of the grain that has not been fixed yet. You can take the chullin out of the storehouse later, when you have the time and manpower, or perhaps wait until you proces and tithe the entire storehouse. In this situation, there may be a way in which you can estmate and need not measure exactly.
Let's look at the following mishna in Terumos 4:2:
One who had his produce in storage and gave a seah to a Levite and seah to a poor man, he can take out (from the storehouse) eight seahs and eat them - this is what R. Meir says. The Sages say: " he separates according to a measure (cheshbon)".
What is this "measure"? There are many explanations. One of the more common ones is that R. Meir says that one does not need to be concerned that the maaser may have been consumed and that chullin cannot be any longer taken off on the basis of what was given to the Levite/ poor man. In other words, the owner can assume that the maaser that was given is still in existence and can take out chullin from storage according to the amount of maaser that was initially separated.
The Sages say that one cannot rely on the maaser still being in existence. Instead one must ascertain what remains and take out only as much chullin as is justified by the amount of maaser still in existence. How does one ascertain this. Some commentators say that this must be known vaddai; however, it may be suggested that the owner can estimate. Without making this post more complicated, an understanding of cheshbon as arising from estimation comes out of how this term is used in two instances in chapter 5 of Terumos.
We return now to our mishnah in Avos.
"do not frequently give tithes by estimation". This is a common example from daily life. This means that one should not get used to giving maaser and leaving its corresponding chullin in the storage house, relying on estimating how much of the maaser is still in existance, when taking the chullin out. The pointt is the same as that on the other two examples in the mishna, that a person should not get used to traveling through life "by the seat of his pants", that one should not become accustomes to estimating and imprecision as a way of life, and that one should pursue exactness and clarity in everything one does.
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