I think the biggest risk is with finding the right assemble of contractors.I have had my share of kicking guys off of jobs threatening to keep tools and wasting money by trying to take short cuts.  

My biggest thing of concern was days on market.

The biggest factor for the high price tag in my opinion is the fact that oil wells are on the property.

I think the largest hurdle to jump is understanding the margins and what a good deal actually looks like.If you can turn up good solid deals the rest will fall into place.

Account ClosedKnowing a little about South Padre,  I would list it with a Realtor for the following reasons:-There is a good chance your buyer will be an older retiree who, while times are changing, will not look at Craigslist, Zillow etc. and would expect a face to face encounter-Other potential buyers will be there on vacation and will have limited time there so have access to a Realtor to show will helpThe goal is to have the biggest pool of buyers possible. 

It strikes me that as a Wholesaler, where your deals come from is the biggest part of it, and just letting someone else do it, is going to limit both parties success. 

However, before I tout my own personal opinion I believe it is prudent to list several of the PROs and CONs first;The biggest PRO is that you can literally rekey the lock yourself in less than 30 seconds.

Isn't one of the biggest dangers and expenses the potential to not sell in the time frame you planned for and end up paying high interest on borrowed money?  

In fact he said the biggest claim he's paid out was a bit over 100k.

My biggest problem with DIY carpet clean is that unless you buy an expensive cleaner, you're doing little more than a regular vacuum does.