Subsequently, you can transition to long-term financing with a cash-out option. 

But if they will be difficult, then it won't be worth it unless the deal is so good that you and the subsequent assignee are fine, sight unseen, which is rare.

There aren't even really separate entrances to the place, unless you count the sliding patio door and the ADU / house are not separated (you can go in between both from inside the house). 

You want to make sure that you can use rental income to knock down your DTI and qualify for subsequent properties. 

When I contacted them subsequently (in 2012 or 2013) about potential roof work, they ended up sending someone from Durable Roofing, which I interpreted as an "overflow referral." 

@Richard Quijano You need a very reliable contractor to handle the construction and subsequent city inspections.

If it's to fix and the subsequently hold, not only do your numbers have to work, but you should have a pre-approval from a reputable portfolio lender that will pull you out of the hard money once the property is stabilized. 

I completely understand the process in a retail build-out (built ins displays vs. movable furniture displays; is the lighting accent lighting vs. base building lighting and subsequently following all the wiring, connectors, j-boxes to the sources, etc).

After you have one property under your belt I’d imagine the subsequent ones would be a little easier as you’ll be able to leverage the relationships you formed doing the first deal.

Unless the previous borrower requests a release of liability, the servicer must process the following exempt transactions without reviewing or approving the terms of the transfer:a limited liability company (LLC), provided thatthe mortgage loan was purchased or securitized by Fannie Mae on or after June 1, 2016, andthe LLC is controlled by the original borrower or the original borrower owns a majority interest in the LLC, and if the transfer results in a permitted change of occupancy type to an investment property, such change does not violate the security instrument (for example, the 12 month occupancy requirement for a principal residence).The servicer must notify the borrower that a property transferred to an LLC must be transferred back to a natural person prior to any subsequent refinance application in order to meet Fannie Mae’s Selling Guide underwriting requirements.FREDDIE MAC TRANSFERSHere is Freddie Mac lookup tool: https://loanlookup.freddiemac....https://guide.freddiemac.com/a...