It is a good question to ask twice:) 

You have to counsel your client to find out what would be the best strategic plan based on their needs and finance. 

Bridge loan, buy a new home first or go with my answer to the similar q

What is their acceptable level of risk? You can always rent until you find another place. You can't wish a sale of your present home once you sign a contract for another one.

Sell first with a home of choice contingency.  Most sellers won't accept a contingent offer in this market.

Many seniors can pay cash after they sell their home but do not have access to bridge financing to purchase another home before selling their present home.

  1.  Challenging as in Sellers market or Buyers market?

  2.  What is their financial position?   Can they afford to own 2 houses at the same time? 

Inna Ivchenko nailed this one!

Depends 

Can they do a bridge loan?  Do they have an emergency place to move to?  I would check out all options.

It depends on the client and their individual needs and resources...why do they need to sell?

Hard decision in a tight market.

Again, it all depends upon their financial situation - if we can be prepared to list and they can carry two mortgages temporarily, we get them in their purchase first, THEN list.

The key is doing so without an contingencies and working hand-in-hand with the lender.

Duplicate.

I've had some who could buy first and then sell. I've had others who had to sell before buying. It really depends on on each individual client and where they want to be and what they are selling.