I own rental property in a single member LLC. This year I paid monthly premiums for individual health insurance. Can I deduct that cost and other medical costs on Schedule C of individual tax return and list expenses and income of rental property on Schedule E, like I usually do. Thanks!

no unless you file sch c/sch se o as a self employer or unless you are a real estate pro filing sch c/ sch se.you need to itemize them on sch a of 1040, so unless youy itemize them on sch a , you can’t deduct it.

I am self employed as real estate investor (on a small scale), but do rentals on Sch E. Can I start doing Sch C as RE investor and deduct medical expenses there, and still do income/exp on Sch E (so I would not be showing income on Sch C). Thanks.

As mentioned previously, aslongas you file Sch E of 1040, no you can’t deduct your med exp on Sch A of 1040.

#2;No. as a r/e pro, if you need to file Sch C/SE, then you MUST file ONLY Sch C/SE ,NOT Sch C and Sch E at the same time;as long as you are in the business of selling real estate, then you would use Sch C of 1040 to report your business income and expenses. If you are in the business of renting real estate properties you own, then the income and expenses are reported on Sch E of 1040; as long as the amount on Sch C line 29/ 31 is $400 or exceeds $400, then you need to file Sch C and also as long as the amount on line 4 of Sch SE is $400 or exceeds $400 then you need to pay SE tax. You must make estimated tax payments for the current tax year if You expect to owe at least $1,000 in tax for the current tax year, after subtracting your withholding and credits ORyou expect your withholding and credits to be less than the smaller of: 90% of the tax to be shown on your current year’s tax return, or 100% of the tax shown on your prior year’s tax return on 1040 line 60. (Your prior year tax return must cover all 12 months.). In this case, as you file Sch C/SE, you can deduct the whole of your med exp on your 1040 line 29 as a self employer filing Sch C/SE and also you can deduct 50% of your self employment taxes on line 27.
Note;in general, The irs says that most individuals renting property to others need to report rental income using Sch E. If you are a real estate dealer who receives income from renting real property or an owner of a hotel, motel, etc., who provides services ,maid services, etc. for guests, report the rental income and expenses on Sch C or C-EZ. If you are not a real estate dealer or the kind of owner described in the preceding sentence, you need to report the rental income and expenses on Sch E. You are a real estate dealer if you are engaged in the business of selling real estate to customers with the purpose of making a profit from those sales. Rent you receive from real estate held for sale to customers is subject to SE tax. However, rent you receive from real estate held for speculation or investment is not subject to SE tax.

Thank you!