Would you sell, wait to get all the cash, and buy the other one, or would you do some transition between that in a way that you would do some overlapping instead of waiting for it all step by step done.

If you can find multiple agents like this, that's better.In no circumstance are you negatively affected by having multiple agents looking for properties for you, so long as you keep the inventory overlap to a minimum and allow each agent to focus on their niche/specialty/geo area of focus.

Baltimore and DC are drastically different markets, and usually does not have an overlap of people investing in both even though they are very close. 

There is overlap but it's not necessary to have that background to be successful. 

Schedule two meetings with GCs (if you are still looking for one to do the work) during that time but don't overlap those meetings.If I am not doing any work that requires full building plans stamped by an architect and engineer:I try to schedule closings in the morning and on a Monday or Tuesday.

I would focus on that area of overlap as it will always be sought after.

I don't want gaps or overlaps in my coverage. 

It is very hard to find tasks that don't overlap.

You can pull out that piece of trim that's there and see how much it overlaps the floor to determine the dimensions of your new trim.  

I thought I had “Builder’s Risk” coverage…Even if you have the appropriate coverage for a property undergoing renovation, the reason for these exclusions is to avoid an overlap of coverages.