How To Structure My Properties (LLC and write-off question)

[Kenneth Woodall]

I own a few properties (SFR, duplexes) in various states: CA (2 multis), FL (2 multis), TN (1 SFR). All are sole-proprietorship. Some are paid off, others have mortgages.

1: How would you structure these in LLCs (I know the answer varies, just looking for your personal opinion and why)

2: I travel to different sites looking for new investments. How can I write these off on my taxes? As sole-prop, I can only write off travel as misc expense which tends to be a red flag for IRS.  

I manage my properties online myself. I have a lot of write-offs like internet, office, websites, etc. However, splitting these write-offs into individual properties isn't realistic. Can I create a "management company" LLC that I own, then pay that LLC from each property, then pay myself from that LLC?

3: Main question: considering all the above info (I own properties in multiple states that I manage myself), what's the best structure to write off my expenses in a way that minimizes any IRS red flags?

Thank you!

[Ashish Acharya]

Originally posted by @Kenneth Woodall:

I own a few properties (SFR, duplexes) in various states: CA (2 multis), FL (2 multis), TN (1 SFR). All are sole-proprietorship. Some are paid off, others have mortgages.

1: How would you structure these in LLCs (I know the answer varies, just looking for your personal opinion and why)

2: I travel to different sites looking for new investments. How can I write these off on my taxes? As sole-prop, I can only write off travel as misc expense which tends to be a red flag for IRS.  

I manage my properties online myself. I have a lot of write-offs like internet, office, websites, etc. However, splitting these write-offs into individual properties isn't realistic. Can I create a "management company" LLC that I own, then pay that LLC from each property, then pay myself from that LLC?

3: Main question: considering all the above info (I own properties in multiple states that I manage myself), what's the best structure to write off my expenses in a way that minimizes any IRS red flags?

Thank you!

What you described are not red flags.

Yes, creating an operating/management entity will make it easier but will not give your significantly greater deductions. You are entitled to same deductions without it.