Trust, but verify.I was looking for someone that already is or on their way to being financially free, someone who I can connect with personally, and who is willing to teach/coach me in my specific circumstances.

Some require you to have experience, some require you to own a primary residence, some don't require either under certain circumstances.

I also don't know all your circumstances ... but I provide the source for you to dig into it deeper down below.  

There are very special circumstances where a lender will count projected rents by the room.

But the best ways to get started are, in my opinion: 1) save up enough for a 10-20% down payment and then save a lot more on top of that for reserves, overages, and any unforeseen repairs.    2) have your financial house in order and have credit above 700 to get more favorable rate and terms from lenders.   3) speak to a loan officer that is experienced with fix and flips and get the necessary documents together for a pre approval (typically not much required, usually a valid ID, LLC docs if any, and two months of bank statements showing funds for down payment and reserves). 

My question centers around why and how could that be  (not that it can’t be… but can you change your circumstances while still keeping the rentals?)

It is the only option, save for some highly unusual circumstances.

(Depending on deal , state , circumstance ) Consider actually purchasing the property and then selling days or weeks later instead of a double close if you run into that issue.

That is a very unique situation that no other contractor would ever offer you, so IMO, given your circumstances (assuming you are able and qualified financially and won’t be house poor) I would take your buddy up on the multi construction seminar.

The renovation costs may include a contingency reserve and renovation-related costs.Contingency Reserves:Contingency reserves 10 % required for any unforeseen cost overruns that may occur during construction.Unused contingency reserves that were financed into the loan will be applied to the principal balance of the loan.