Should I be worried that I won't be given a receipt if I pay with cash?
If this is because he wants to avoid paying taxes, will I get in trouble if I agree to have him work on my vehicle? You should check your state and local sales tax laws to be certain, but in my state you have no liability if he does not pay his taxes.  That's his problem, not yours.  The biggest risk for you is if something goes wrong, you have no proof that the work was ever done, so it's possible he could deny that any transaction ever took place and refuse to correct it or refund your money.  So at worst you're out what you paid for the service, plus what it would cost you to fix it if you needed to and chose to do so.  If you don't want to take that risk, then insist on a receipt or take you  business elsewhere, but there's no criminal liability for you if he chooses not to report the income. EDIT Be aware, though that state tax is levied at the state and local level, so the laws of your individual state or city may be different. "There are number of reasons why someone doesn't want to give you a receipt for cash payment. Anything ranging from not wanting to pay taxes, to being able to deny you gave them money for service in the event you're not happy with the service and ask for money back. You won't get in trouble for giving him cash, however you should be worried because any ""reputable"" person providing any type of service/product will provide a receipt regardless of payment type." In some states, it is your responsibility to pay the sales tax on a transaction, even if the party your purchase from doesn't collect it. This is common with online purchases across state lines; for example, here in Massachusetts, if I buy something from New Hampshire (where there is no sales tax), I am required to pay MA sales tax on the purchase when I file my income taxes. Buying a service that did not include taxes just shifts the burden of paperwork from the other party to me. Even if you would end up saving money by paying in cash, as other here have pointed out, you are sacrificing a degree of protection if something goes wrong with the transaction. He could take your money and walk away without doing the work, or do a sloppy job, or even damage your vehicle. Without a receipt, it is your word against his that the transaction ever even took place. Should you be worried that he is offering a discount for an under the table transaction? Probably not, as long as you don't take him up on it.
"You could always put cash in an envelope and mail it, with no return address on the envelope. Any form of anonymous donation that I can think of has the risk that if the money is intercepted and stolen, you'll never know. Also, you won't get a receipt that you can use for tax purposes. You could try sending this organization a note saying, ""I think you're doing great work, but this donation was a one-time gift. Please take me off your mailing list."" I don't know if it would work, but it's worth a try. By the way, the problem is worse than you think: charities share mailing lists. Once one charity has your name, they'll often share it with other related charities. For example, I give to the Catholic Family Association even though I am a Protestant -- I think they're doing good work that Catholics, Protestants, and people of many other faiths could support. But over the years I started getting fundraising letters from other Catholic charities, and then from groups trying to spread Catholicism, and now I'm getting mailings from groups whose stated purpose is to oppose Protestants. I laugh and throw away the letters, but I know some people get really bothered by this sort of thing. ""I'm pretty sure that the total cost of the mailings including postage has now exceeded the $20 I donated."" I've occassionally thought of sending some trivial donation, $5 or $10, to some political or activist group that I totally oppose, just so they'll spend way more than that over the course of the next few years asking me for more money. :-) Plus, they'll send me letters that will tell me what the opposition is up to." It's incredibly difficult to beat the market, especially after you're paying out significant fees for managed funds. The Bogleheads have some good things going for them on their low cost Vanguard style funds. The biggest winners in the financial markets are the people collecting fees from churn or setting up the deals which take advantage of less sophisticated/connected players. Buy, Hold and Forget has been shown as a loser as well in this recession. Diversifying and re-balancing however takes advantage of market swings by cashing out winners and buying beaten down stocks. If you take advantages of general market highs and lows (without worrying about strict timing) every few months to re-balance, you buy some protection from crashes in any given sector. One common guideline is to use your age as the percentage of your holdings that are in cash equivalents, rather than stocks. At age 28, at least 28% of my account should be in bonds, real estate, commodities, etc. This should help guide your allocation and re-balancing strategy. Finally, focusing on Growth and Income funds may give you a better shot at above S&P returns, but it's wise to hold a small percentage in the S&P 500 as well. "As others have pointed out, it's all about a fixed, small cost versus the potential of a large cost. If you have insurance, you know you will pay a fixed amount per month. There is a 100% probability that you will have to pay this premium. If you don't have insurance, there is a large chance that you will have no cost in any given month, and a small chance that you will have a large cost. Like my home-owners insurance costs me about $50 per month. If I didn't have insurance and my house burned down, I would be out something like $100,000. What's the chance that my house will burn down this month? Very small. But I'd rather pay $50 and not have to worry about it. On the other hand, I just bought a filing cabinet for $160 and the store offered me an ""extended warranty"" for something like $20 a year. What's the probability that some accident will happen that damages my filing cabinet? Pretty small. Even if it did, I think I could handle shelling out $160. I can imagine my stomach in knots and lying awake at nights worrying about the possibility of losing $100,000 or finding myself homeless. I can't imagine lying awake at nights worrying about losing $160 or being force to stuff my files under the bed. I'll take my chances. When I was young and had even less money than I have now, I bought cars that cost me a thousand dollars or. Even poor as I was, I knew that if the car was totaled I could dig up the cash to buy another. It wasn't worth paying the insurance premium. These days I'm driving a car that cost me $6,000. I have collision and comprehensive insurance, but I think it's debatable. I bought the car with cash to begin with, and if I had to I could scrape up the cash to replace it. Especially considering that my last payment for my daughter's college tuition is due next month and then that expense is gone. :-)" "I would write them a check or give them cash money. There are payment receipt forms available online, you can print one of have them fill it out and sign it. Just google ""private party receipt"".  Money transfer (via bank account or Paypal) is also an option, but in my opinion it's more convenient to meet up and handle it in person. If you want, you can have them meet you at a notary public's office (your local bank branch should have one) and have the receipt notarized. I don't think it's a scam, but make sure you are paying the right person." Generally, I consider it bad etiquette to inconvenience others.   I would recommend cash for small purchases. Try to offer as close to the required amount as possible.  Don't pay with several dollars worth of change if you can avoid it. You shouldn't need to carry a lot of cash.  When you do don't make it obvious. As I replied to someone else who said that:  I'm often having to send stuff with the check. Paperwork, a bill etc. While that would work to a person who knows me, it's usually not going to work with a business or government who needs to know why I'm sending this check. "Let me just add that while you don't need to write the date received on the back of the check, you could. Why? Let's say someone was late in paying you and you wanted to document the fact that they were late. I've had late-paying customers send me a check dated on the due date but really they just pre-dated the check and sent it 60 days past-due. So let's say I want to establish and document the pattern in case it becomes a future legal issue. When you deposit or cash a check, an image of the front and back is made and the person or company who issued the check will have those images stored as part of their transaction history. (It used to be that the original, physical, cancelled check was returned to the payer, but that was another era.) So write the date received on the back next to the endorsement, endorse the check, and take a photo of the front and back (along with the postmark on the envelope) to document that they are a late payer. This way, if it ever becomes a ""he said she said"" issue you can easily show they have a history of paying late. If the payer looks at their check images they'll see your received date note next to the endorsement. Granted, this is a lot of trouble for a unique situation. In 20+ years of running a business I've actually had the foresight to do this a handful of times with habitual offenders, and in (only) one case did it come in handy later on. But boy was I glad to have those photos when I needed them." Cash-back also lets the store turn hard currency into an electronic transfer or check, which reduces the hassle/risk of hauling bagfulls of cash to the bank. (The smaller stores I've spoken to have called this out as a major advantage of plastic over either cash or checks. I'm assuming that the problem scales with number and size of transactions.)