Advertising copywriting legend Gary Halbert used to say that if he were to open a restaurant, he'd want a list of starving people (with money). 

My day to day "job" is website development and copywriting.  

However, I would suggest that you look for a different target market than the affluent and, as you mentioned, study Dan and others' copywriting material.

The followup system when a seller callsIf you're not a great sales copywriter and don't know the proper strategy on how to make a direct mail piece work in your market, it's likely not going be profitable. 

What's your biggest hurdle when writing real estate ads?

Hopefully Erica above can help you out, with some proper targeting and copy writing in your listing.

Old copywriter's tactic: Add a P.S. that states an important benefit, such as, "I'll pay cash and no inspection is required!"

Have you considered the copywriting you use in your marketing? 

Post looks like it was written by a copywriter out to sell something.

I would also suggest reading about copy-writing to improve your writing as well as working with an illustrator (get them through Fiverr, Elance, etc) to make your document look more appealing.