It sounds scary, but it is setup that way as a consumer protection. 

I know this sounds like a stupid and confusing post, but Im trying to make sense of it all and I am on the fence about selling my house or a HELOC.

Sounds like a headache. 

Curious to know what insurance sites have been effective for you & what statr are you located in? 

.- At the surface it sounds like a great opportunity, but I think there needs to be some more digging into the numbers to understand if its worth it at that price, and what the risk profile is.  

Sounds like a good candidate question for Tax Tuesdays.

Tied to this is the fact that it is very hard for us to make informed decisions about making purchases in markets we are unfamiliar with, given the normal ebb and flow of real estate activity.That said, I am not raising this primarily to criticize these companies, but rather to focus on the practical effect of what they leave out.

I'd be talking to at least 10 national lenders from biggerpockets and have your land appraised. you better have permits in hand, entitlements. complete, etc. sounds like it's too early to be talking about financing. 

That's also an option to temporarily bridge the gap of quitting a full-time job.It's also important to be making enough on your properties so you're cash flowing enough so you can buy more property - sounds like common sense but as mentioned you can always freelance or do something you enjoy part-time to bridge the gap in pay.

So that sound a lot like $200K a door.