But there could always be circumstances where a shorter or longer hold period would be appropriate to demonstrate your intent.

One tip is closely track your interactions with any potential investor, but in any circumstance when you enter into the syndication/private investor arena you need to be familiar with the rules so that you do not blow an exemption or break the law.

@Alexander Felice agreed, all circumstances are different.

Low-ball offers can be effective in limited circumstances - Off market ( which are typically uneducated/distressed), bank owned, and really weird properties.

We have bought land before it goes to Auction before, but never under these circumstances.

In a way, we're trapped in our current home even if we own it free and clear, which is an odd circumstance.

I have an LLC set up and my question is twofold. 1) I understand putting this property into the LLC could trigger the due on sale clause, but my mortgage says it will allow "under certain circumstances" the transfer to another person.

Under the circumstances I doubt there would be any pushback from agent or broker on a request to sever the relationship early.

Would I be able to qualify for a 203K under these circumstances? 

Depending on the amount of your profit and the size of the down payment you could simply do the 1031 on the cash you received and take the note as boot.In the right circumstances if you've got access to cash doing a 1031 combined with owner financing can be a great way to multiply your cash flow while deferring a lot of tax.