If there over 2 years with a large gain, it would affect my decision.

I am definitely needing mentorship, in hopes to gain enough courage to finally stop torturing myself and begin my dream.

Personally I don't put much weight into that.  

To all:I recently finished a flip, after it was done I had a friend who saw what we did told her sister (who apparently is in the market for a new house this summer) and now the sister wants me to do the same for her....

I have been gaining more and more interest in the idea of investing real estate, particularly multi family properties.  

It becomes hard to prove to the IRS what is inventory and what isn't.If there is more than one shareholder of an LLC it is taxed as a partnership UNLESS you are in a community property state.You need to understand that an LLC DOES NOT EXIST as far as the IRS is concerned: http://www.biggerpockets.com/forums/12/topics/7605...You can flip in a C-corp or s-corp and then distribute the income or even loan from there.Personal Holding Company Tax (PHC Tax) is a 20% tax on a corporation that holds passive based income that GROSSES more than 60% of the income.C-corps have NO CAPITAL GAIN RATES.Here is a thread on Real Estate in a C-corp and trying to get it out: http://www.biggerpockets.com/forums/51/topics/1057...

2) My understanding is that as long as I return all the profits back into the Roth IRA I do not have to pay any capital gains tax (or any other tax), correct?

Matt Gaines Best advice I can give you is for you to find a good turnkey company from referrals from actual investors who have actually used them, and actually own property in that market.

J Beard I intended to keep it for 2 years at least to avoid any capital gains taxes.

The property is still considered a primary residence by the 2-out-of-5-years rule, so I will only owe capital gains taxes on recaptured depreciation.In 2015 I made a profit and will depreciate that year up to the limit.