Hi all, I am new to the board and have a bit of a complicated question regarding mileage deductions. Here is my situation:

I have several business interests...

• Biz 1: (Sched C) One of which is run completely from my home office (yes, a separate space used only for that business!).
• Biz 2: (LLC, multi-member) I also have a business for which I rent office space about 3 miles from my house. (I have employees and a biz partner that works from that location.)
• Biz 3: (LLC, single member) ...and another for which I rent office space at a WeWork co-working location approximately 25 miles away from home. I also use this space to meet with clients from all three businesses when necessary.

My typical work day generally goes like this: Start the day in the home office working on Biz 1 tasks, though I usually spend 30-45 minutes checking emails for Biz 2/3. After that, I am in my car driving to one of three places. Either to meet with clients/vendors/etc. for Biz 1, to the office for Biz 2, or to the office for Biz 3, where I may or may not be meeting with business contact from Biz 1.

My question: What the heck is actually deductible per IRS rules?

Bonus question: On Saturdays, I sometimes drive to a golf course with the intentions of playing golf. But sometimes (more often than I'd like, actually!) I run into a client at the golf course and we spend an hour meeting over a business issue. Then, maybe we play golf, maybe not. After which, I drive back to my home (office), where typically the first thing I do is spend a few minutes working on whatever was discussed. Is any mileage from that trip deductible?

Super bonus question: I have approx 300 miles from my parents. Last time I visited them, I met their neighbor, a nice retired lady with years of administrative experience. From time to time, I upload audio files to her to transcribe. I pay her as a 1099 contractor, and it's generally small amounts of work. Once in a great while, I have boxes of surveys, the results of which need to be entered into a database. Usually, I ship these to her via UPS, but what if I drove them to her in my car. Should be a deductible trip, right? What if I visit my parents after I drop the boxes off? How about the trip back? What if I was going to see my parents anyway, and just wanted to save on shipping charges?

Ok, that's a lot for my first post ever, but I've read some great responses here to other questions, so I thought I'd fire away!

Thanks in advance for any answers.

My question: What the heck is actually deductible per IRS rules?=====> Expenses for travel between your home and other work locations are deductible if your residence is your principal place of business.you must establish that your home is your principal place of business. This is pretty easy if your home is your only place of business, but if you have other places where you work, you must show that You use it exclusively and regularly for administrative or management activities of your trade or business, AND You have no other fixed location where you conduct substantial administrative or management activities of your trade or business and then since your home is your biz place, you can claim your auto exp for ? After that, you are in the car driving to one of three places. Either to meet with clients/vendors/etc. for Biz 1, to the office for Biz 2, or to the office for Biz 3, where you may or may not be meeting with business contact from Biz 1.?



Bonus question: On Saturdays, I sometimes drive to a golf course with the intentions of playing golf. But sometimes (more often than I'd like, actually!) I run into a client at the golf course and we spend an hour meeting over a business issue. Then, maybe we play golf, maybe not. After which, I drive back to my home (office), where typically the first thing I do is spend a few minutes working on whatever was discussed. Is any mileage from that trip deductible?====>I do not think so; Basically, you have to play in connection with business activities, but that?s pretty easy to pull off. If you can demonstrate a trip (or a portion of a trip) was taken for the ?pursuit of business? then, you can deduct your costs of getting to and from the destination and any business-related expenses you incur at the destination, basically aslognas you have ?substantial business discussions? with prospects, clients, customers, or employees in person, over the phone, or by email that you could instead conduct at a golf course?
If so, you can deduct 50 % of what you spend on golf and meals (plus the roundtrip mileage) as long as you conduct your business discussion before or after you play and you conduct it in a business setting, such as a quiet and preferably private space inside the clubhouse.


Super bonus question: I have approx 300 miles from my parents. Last time I visited them, I met their neighbor, a nice retired lady with years of administrative experience. From time to time, I upload audio files to her to transcribe. I pay her as a 1099 contractor, and it's generally small amounts of work. Once in a great while, I have boxes of surveys, the results of which need to be entered into a database. Usually, I ship these to her via UPS, but what if I drove them to her in my car. Should be a deductible trip, right? What if I visit my parents after I drop the boxes off?===>no you can not claim the miles to see your parents. Not biz related car expenses.

How about the trip back? => as said basically you can claim biz related auto expenses aslognas you pay her as a 1099 contractor and she files her return to report her self employment income 1099incoem I mean on her federal/state returns.



What if I was going to see my parents anyway, and just wanted to save on shipping charges?=====>anyway only biz related car expenses are deductible. Car expense to see parents are not biz related expense.