You are making a grave mistake by looking too far ahead right now, without capital, because that usually means you aren't focused on upgrading and securing your first asset.

If you have the go-ahead from the county, I would get at least 3 bids from contractors to see if installing a shower is possible, making entrances easier, and generally improving the basement to be more complete overall.

Go ahead and list whenever you are ready. 

You will have to get ahead of the price drops as what you are seeing is a lag metric.

The walls can't be cracking and 1990's beige when you installed brand new hardwoods throughout.And, while new cabinets and counters and appliances are nice, if they are not well laid out, or you jam an island into a space that does not allow for stools to be pushed out, or the oven door to open because it hits a cabinet pull, that new kitchen is meaningless. 

Enough to justify using him every time he is available (and he has bumped me ahead of other customers because of my repeated use).  

I went ahead and pay the retainer fee to have anna as my retainer. so let see how this plays out

No real need to pay a broker fee if you are already ahead of the curve and have found/posted on BP!

Your suggestion is a heads I win, tails you lose.

Zillow will also push your listings onto Trulia and HotpadsMLS.