There are many different taxes involved. An accountant can pay some with no additional input, but not others.
For example, property taxes are based on the property and not the owner and conceivably one may pay them without ever being in contact with the owner.
However income taxes are based on income, and without knowing the income it is going to be impossible to file adequate tax returns and pay the correct amounts. Given your Bob has significant assets in the endowment it is very likely that they generate some income (interest, dividends, rents, royalties). If they set up an entity - they'd be getting some distributions from that entity. The Internal Revenue Code, and the Treasury Circular 230 (31 CFR 10), impose penalties for an accountant and taxpayer filing fraudulent returns.
Note that income can be in terms of barter as well. If Bob hunted a deer but wants milk - Bob gives deer meat to Candice and Candice in return gives Bob a bucket of milk. Bob just sold an asset, gaining the value of the milk minus the expenses of acquiring the deer meat prorated to the portion sold (part of the depreciation of the rifle, ammo). The fact that they live in a community is irrelevant (Bob and Candice being married is relevant though, if they are).
Even Alice's stipend may be an income to Bob. Alice's compensation may or may not be deductible (currently is not, but in 1980's may have been), but that would be under certain conditions as an itemized deduction.
If the question is whether the Bob kills the deer illegally and then appropriately reports the income would create liability for Alice - then it depends on the circumstances. There's no "accountant-client" privilege, but there's also no general requirement to report past crimes. Being the filer and Bob's representative Alice may end up being asked and if asked - will have to provide the information because... no privilege. Unless Alice is an attorney, of course.