My plan was to keep the condo as my residence, but after a year, refinance to fund a down payment on a multi-family property, either out of state or in the surrounding NY area.

Some of the discounts are good, but just be aware that you will be paying a payment processing fee on top of the discounts. 

Then if/when another good deal comes up, you can approach a lender and look at leveraging either of the properties in order to fund the down payment of the new property.

This lead to piecing together payments here and there and drastically slowed the construction process and major cost overruns.

Know that every long term lender will require a survey and if something comes up on it when you are trying to sell or refi, you could get stuck in hard money without an easy or quick way to get out.Is there a pre-payment penalty?

So the problem is you wont be able to source the down payment as coming from the seller (most likely), but you can certainly add as many junior lienholders as you like, after the fact.

NONE of the money raised from the auction of a 2nd goes toward the payment of the 1st (that is why they call it "subject to the first")4.

They have failed to renew my entities with the Secretaries of State multiple times, have billed me wrong amounts, and GREATEST OF ALL, have cost my business ~$50K in cumulative TAX PENALTIES due to negligence in filing for a tax extension, failing to walk me through my tax filings and needed payments, and failing to file an abatement promptly.

You have to weigh the benefit of the insurance claim payment versus potentially having your carrier cancel you and perhaps get black-balled by the insurance industry.

Honestly is better spent as a down payment on a second building.