Working and Business
Collecting debts: It is permitted to collect money of a loan during Chol Hamoed. This applies whether the borrower is a Jew or gentile. [This applies even if one is able to collect the loan also after the Moed.] It is, however, forbidden to collect merchandise in exchange for the loan, unless one may not be able to collect the loan after the Moed. If one is owed money for a service or sale of a product, it may be collected during Chol Hamoed if the client/customer was already billed for payment prior to the Moed. If, however, the client/customer was not yet billed for payment, then one may only bill him to collect money during the Moed if one may not be able to do so afterwards.
The custom today: All the above is from the letter of the law, however, the custom today is to collect all debts during the Moed, as it is all considered today as if one may not be able to collect it after the Moed. The Poskim justify this custom.
May one build an item on Chol Hamoed for the sake of his business which will remain open during Chol Hamoed due to Davar Haveid? If building the item is necessary for bringing in income that is defined as Davar Haveid, then it is permitted to do so. Nevertheless, it is forbidden to schedule to do this Melacha during the Moed, and one must initially do so before the Moed. If one intentionally scheduled to do so during the Moed he may not do so even in a case of Davar Haveid.
May one buy or sell on Chol Hamoed? It is forbidden to buy or sell on Chol Hamoed. If, however, one has an opportunity to bring in a large income through the sale, he may do so in private. In such a case one is to spend more money than he originally intended for his Yom Tov expenses.
May one purchase items on sale during Chol Hamoed? Yes. If the sale is limited to the days of Chol Hameod, it is permitted to purchase the sale item during Chol Hamoed.
May one buy toys for children, and presents for people during Chol Hamoed? Some Poskim write it is permitted to buy presents for children during Chol Hamoed due to the Mitzvah of Simchas Yom Tov. This applies even if the item is not required for Chol Hamoed.
May one buy things for the Moed in a Jewish owned store that is open without following the Halachic regulations? Seemingly it is forbidden to do so.
May one buy clothing which are needed for the festival during Chol Hamoed? It is permitted to buy clothing during Chol Hamoed if they are needed for the Moed or for Yom Tov, even if they are needed for Yom Tov Sheini.
May one lend money to a gentile on Chol Hamoed? One may make an interest loan to a gentile customer on Chol Hamoed if the gentile is a previous customer. If the gentile is a new customer, then although it is permitted to give him an interest loan nevertheless, he is to use some of the interest earned towards expenditure on Simchas Yom Tov.
May one hire a worker during Chol Hamoed to work for him after the Moed? Yes.
Is it better to take a Jewish or gentile taxi driver during Chol Hamoed? It is better to take a gentile taxi driver, as in general a Jewish driver is not allowed to work during Chol Hamoed.
May one cash a check on Chol Hamoed? One may not cash a check on Chol Hamoed unless he is unsure whether there will be money in the account of the check after Yom Tov. [Likewise, if one needs the money for holiday needs or to cover payments that are due then he may cash the check.]
May one make a deposit on Chol Hamoed? It is forbidden to do so due to the business prohibition. If, however, one fears the money being stolen or needs to cover checks that have already been written out.
May one pay bills during Chol Hamoed? Some Poskim rule one may not do so. Others rule it is permitted.
