We filled in a pool, that had a cement apron and vinyl liner,, we put back in partial clay and sand, it would have been better if we had used all sand.. we would get standing water after large rain storm.. city made us remove all concrete, mechanical, and liner only thing they would allow was small amount of loose chunks of concrete size of basket ball,  other wise it all went. it cost us about 4 grand to fill in the pool.. 

Being off by $125 in insurance on a property of that size could really affect things.  

I've been thinking a lot about down sizing. 

Now I know this is a very broad question and there is so many variables to give a honest answer, such as far as how they financed the project, what they are building, the size of the property and a ton of things more to consider.But for this post lets just use developers who build luxury spec homes. for instance we can use a big market like Los Angeles, how much do they developers really make who buy a single family house and develop a new luxury modern home and then put it on the market for Millions and millions.Seems like there is a ton of risk involved with it, and also seems like they rely heavy on financing with both debt and equity component.

I am on the HOA board of a smaller sized Condo Association; 38 units.

Sounds like what happened with yours, you can easily tell by the size of the roach. 

This thread contains a longer list of specific questions you can ask: How to Vet a Private Lender You'll find that lenders come in different shapes and sizes.

Right now homes are flying off the shelf in the suburbs like yours, you shouldn't have much of a problem selling.The fact that you have many showings tells me that buyers are interested but turned off either by layout, furnishings, or size.

I'm near California and Cermak and I've never seen one of any size sell for more than 400k near here.

You could also pursue a reverse exchange if the size of your gain warrants it.