Lots of small details I have played out in my head and could expand upon if need be.

Chris,My difficulty with selling if your are still looking to be a buyer with the cash proceeds is that you are playing both ends of a hot market which nets out.With regards to your question on determining a price, you can look at comps in your area or reach out to an agent if you have one.Real estate is very much a numbers game in my opinion.

If offer is accepted, inspect property.7 - If property inspection shows actual rehab needed "plays nice" with analysis rehab, then buy property,  If actual rehab isn't what you instructed your REA to ONLY bring you, then withdraw the offer.This takes far less time for the REA since I'm only making inspections on properties I like. 

I'll probably order Jeff Booth's book, though I'm betting the big systemic issues he's addressing are more likely to play out over a very long period-- throughout my grandchildren's lives. 

From all the chatter I hear from various real estate investment moguls and my mentors regardless of market is the REI play for the next little while will be in the suburbs.

That's the sandbox I want to play in (or at least explore).

The offer does have a financing clause, but I’m not clear if it would be in play here.

It can be frustrating waiting on a reply or a call that will never come, but it's also pretty low effort and easy to do en masse.

A “retainer” has never ever come into play.

I would like to buy cheap plots of land in good locations, have an architect draw of plans for a triple decker (I am in Mass so anything above a 3 unit would require an elevator), finalize through the approval process, and sell the land and drawings to an developer.