When you sell a rental property at some point in the future (at least a year out), this is not viewed as a flip transaction, but rather just a reallocation of the IRA from holding passive real estate to holding cash.Your example of buy, fix, rent for 3 months, then sell would likely be viewed as a flip, especially if you repeated this pattern with multiple properties.The IRS does not define a "flip" in clear terms, but has a full set of measures they would apply to real estate transactions to determine whether something is a passive investment or a trade or business activity similar to competing commercial enterprises.  

Another town listed on your profile that I'm not familiar with, I see a pattern here!

See a pattern developing?  

For example, sometimes if you look at the listing history for a stale listing, you can see a pattern ... as in, the seller/agent has reduced the list price by $10k every month it doesn't sell for the last 3 months ... then, if you see a pattern like that you can get a feel for if/when it will get down to the ballpark it needs to be price wise ... make a mental note to check back around then, and you can then put an offer in the night before you expect them to drop their price again, with the anticipated price drop, plus an additional smaller price drop to get you a great deal ...

@Todd Dexheimer, you'd better be knocking on wood when you say that:)I just did some cross sectioned analysis for a client based on income and appraisal taxation coupled with growth patterns.  

I experienced a 4 month vacancy in one unit, which obviously hurt my return, but never even came close to cash flow negative.I'm bullish on the long-term appreciation of that area over say, a 15-20 year timeline (which works for me given my age), because I understand the gentrification patterns in Chicago and I know there's no other direction for the money to go. 

Good call Jack.On every forum I post on, when I go through the posting history of anyone I have an issue with, I find a pattern of this type of stuff....You're totally right.

Not cheap but gives you an idea of what you can do just by changing your pattern.

For the major project I had them handle, replacing worn out carpet with Vinyl (Wood Patterned) Flooring I was quoted in writing $2,100 "out the door." 

I haven't observed any discernible pattern, seasonal or otherwise, when it comes to a lull in competition for even slightly below market or undervalued properties.The further you go outside of the core, the less appreciation you will get.