Hey James, I'm sure you've found a solution by now considering this post is 2 years old, but for future reference here is what I have found as far as software solutions for managing a handful of rehab projects at once.Construction/Rehabbing Specific PM Software vs Generic PM SoftwaresWhen choosing your software solutions you will need to decide if you prefer a house flipping software that is specifically built for managing a house flipping business or use a generic project management software.  

Should I do a longer write up on it/other deals i've done?

We wish him the best success with this property and his future in real estate.

@Chris Kay beleive you can do DSR loans without a job as they qualify the property, not the borrower.You'd still need 20-25% down though.That's where you have a decision:- Pay down the mortgage, setting yourself up for a future refinance to free up your VA Entitlement.OR- Save up for your next acquisition.Only YOU can make that decision as you have to be comfortable with the increasing debt-load risk and the additional time to manage everything.

Are you doing the interior TI build out or are you just building the shells and the future tenants will be responsible for building out their units as needed? 

And agree that any prediction is speculative because obviously know one can predict the future.

Networking with luxury RE brokerages will probably fast track you as well. 

I understand that if I rent this ADU out, then I can have a tax write off on the mortgage payment and insurance payment for the the ADU's sqft portion.

In the future, and this goes for all househackers renting a room in your own home, you can choose to use more discretion when picking "tenants" because they're legally seen as roommates FYI.

Don’t forget to plan for the future, maintain a healthy work-life balance, and celebrate small wins along the way—it’s all part of the journey!