Propose Short Sale Deal on Property not In Short Sale Process

[Ying B.]

I have a scenario to run by you regarding a property I would like the seller to consider a Short Sale:

A 5 BR 4 Baths with unfinished basement property (in a school district rated 9 out of 10) was sold in 2007 around $350K. The owner had been in pre-foreclosure but then was able to do loan modifications and property was listed as a regular sale for 309K (3+ months ago) and in Dec 2015 reduced to 299K. There was another short sale on the same street closed at $235K after 90 days on open market as an approved short sale to begin with.  I spoke to the listing agent 1 month ago and asked if they could consider an offer in the range of $230K (cash offer) and she said the owner can't at this price and also did not want to do Short Sale and that the Owner rather let it foreclose then going through a short sale.  I shared with the listing agent that people may change their mind and please keep my (at the time just verbal) offer in mind if they want to pursue with me.  I also gathered that it is possible for the owners to sell around $270K at that time but at $270K it does not make sense to me as an investor as the property need some work and it is an area we don't see appreciation although it is the best school district.  Additionally, there are new constructions in that S/D that range 300K to 350K and it is winter so the sale has been slow ever since December 2015.

It has been 1 month after I spoke to the listing agent and house still unsold and I doubt it will sell before Spring comes. I am counting on the owners getting hopeless and is willing to entertain short sale idea but I need to know if I should contact the listing agent again so she does not feel I going behind her back.  I don't know if she has expertise to do a short sale and not sure once owner pursue short sale if the listing agent will be appointed by the bank.  Should I find another agent who has had success on the Short Sale listing side to do the communication for me? I read about the ramifications of short sale on the seller such as sale price is considered taxable and some damage to credit.  I feel I may not want to be the one who guide owner through this complex process due to liability concerns (if I took them on a path they later find detrimental to them, it is not a good situation).

My bottom line is the property is attractive at the $230K range and I need have a couple of game plans whether involving agent, lawyer or any RE professionals or do it on my own. Can you give me your input?   My plan if I get this property is to live there for 2 years and sell to avoid capital gains.   Considering how difficult to find deals as the general consensus on the forum, this strategy of identifying short sale opportunity may work but don't I need an effective team to help me get it done?  Thank you.