I am new to vacation rentals but have numerous long term rentals.  

I am probably pre-rationalizing to justify a giant apartment in a war zone. :)

I think alot of the answer depends on your intent when purchasing the original property and numerous other factors as outlined in this article;Forbes Article on Cap Gains vs IncomeI would recommend getting a trusted tax advisor involved sooner rather than later. 

Amit, I have done numerous frame work.

You have to be careful about this throughout the City of Indianapolis, but I have seen it specifically in this neighborhood on numerous occasions.

Here's another suggestion that I have forgot to mention numerous times previously. 

They will usually list numerous places and you should be able to get a good sense of the market.

Well I have 5 houses that I bought for 15,000 and there worth about 35,000 to 42,000 I was think of avoiding in a bundle and expanding those 5 one by one or package deal into a few more bigger deals hopefully multi double plex and in an better area cause all my rentals are in war zone

He's been warned by the landlady and the police, numerous times, to leave me be, and has yet to do so. 

We received 2 offers (one actually came before the open house), which created a small bidding war.