Five months after the original post, do you see housing prices continuing to soften or have things started to stabilize now?  

Now with the market softening, this strategy has quickly evaporated and is no longer viable. 

If you are a strong negotiator you will get close to what you want to pay or walk away from the deal without giving it a second thought.Spell out on paper why your offer is where it is to soften the blow to the sellers agent.

We are now past the Two month point so feeling it was overpriced In my opinion and wanting to narrow down the issue, I had an appraisal done and sure enough, the appraisal came back $30k below list price, I said lets list it really close “$5k” to the appraised value, my agent says no one wants to pay list in the DC market now that it is softening and becoming a buyers market, so I will end up selling it below current appraised value if I did that, especially if the buyer ask for concessions which will happen and be expected on a property over 60 days on the MLS.Anyone ever market a property close to or at the appraised value and disclose the appraised number so they don’t get lowball offers?

As most of us are seeing, inventories are either increasing or steady, while sale prices are softening. 1.

Two problems for them:1) This is late in the Tech Unicorn cycle so big Wall Street money starts wondering whether dishing out cash to money burning companies guarantees success.2) Real estate is not retail: their cash offer program means they would carry an inventory that exposes them to being wiped out if/when the market softens.

If they don't, let them go and work your magic.For any tenant you don't want to keep, raise their rent to market rate and make them pay or leave.Do not increase rent in increments to try and soften the blow.

Or should I wait till the market softens?

When things soften up those properties will probably have to reduce rents.   

Or should I just wait until the Fall or Winter, in hopes that the market will soften and I can afford a house hack using a traditional lender?