If there is significant damage typically the insurance company does not cut a check until after the repairs are done - so in most instances if the house had $50k in damage the insurance company does not cut them a check without confirming the repairs were done.

The statement is a bit ambiguous because if you are only referring to a person that has to sign all the deals and be there at close type things, then both the LLC IRA and Solo 401K does not require a custodian to do the deals, both have checkbook control and I can sign for the deals myself in an LLC IRA.

As guru Ron LeGrand says, ask the attorney/"expert" to site actual case reference when making statements such as, "sandwich lease-options aren't legal in (name your state)"...

If you've directly worked with and closed a wholesale deal in CT and found anyone who you would like to refer, please let me know.

The one seller referred me to has a lot of fee, and I feel like it's more than what I would have paid on a new loan. 

In that podcast there was a reference to another podcast by Michael Quarles that I listened to also.

And when people do "subject to" like you mentioned, is it typical for them to quit claim to the buyer but still assume the loan?

Message me and I can refer you to a couple of contractors I know that may need extra help or be willing to take on an apprentice.  

Just vet them well and make sure they come with good references and hopefully you get a personal referral.

I would also be interested in taking a look at that deal you were refering to (for educational purposes).