Yea this is a long-term personal play more than a strict STR deal. 

Possibly break loan covenants and can't cure default, lender takes back property.  

We cannot breach our guests' trust by playing games with them. 

My humble advice to anyone attempting to do creative finance is:Creative finance is for experienced investors who have access to capital if anything goes wrong.Learn the lawsDon't use a contract "off the internet", laws vary by state and are also regulated on a federal levelLearn the financing techniques correctlyDon’t skip parts of the processDon’t ever do a “kitchen table” closingUse the proper deedAn attorney can help you with the legal work, but the rest you are on your ownYour guru will not bail you out“Investing” in someone else’s deal by providing a small 2nd loan so the “investor” can pay for “cash to the seller” and for “closing costs” so he can do the deal is a very bad planKnow what problems can ariseLearn the responses and solutions to problems before they are neededKnow everything there is to know about Title and what that meansKnow who a "protected class" individual isLearn the "back doors"Learn human natureUnderstand timelinesUnderstand regulation enforcement (some of these "mistakes" have a 10 year statue of limitations ( they can charge you 10 years AFTER you do the transaction) and carry hefty fines and possible imprisonmentThe court doesn't accept "I didn't know" for an answer"Know that the source of the lead plays a serious role in some states and federallyKnow how much of a "profit" pushes the boundaries to invite an investigationYou can be sued by the seller if you don’t do things correctlyYou are automatically at fault if an investigator or attorney or regulator gets involved.

The goal of hard money is to get out of it as quickly as possible. 

Because the chances of successfully concluding a wholesale transaction when you lack experience, knowledge and capital are so infinitesimally small that you’d be better off playing the lottery.  

I think the ultimate situation for what I described above (not the plan, but a possible outcome) could look like this:Rent main house by the rooms while constructing ADU.

Given your assumptions, you are not going to be able to get enough of a loan to fully cover the rehab, even with a hard money loan, so you'll need to pull in cash from elsewhere.One possibility is to have your mom sell you the house with a personal loan, not one attached to the property. 

My biggest conundrum now is I want to be my own GC because even when I play with smaller numbers they’re still out of reach for me to be able to attain this goal and afford the monthly mortgage with taxes and insurance.

The Wow ShotWhy it works: Features the unique element that will catch guests’ attention.How to nail it: Highlight a hot tub, pool, view, or quirky design feature.Example: This listingAI’s Role in Airbnb RankingsAirbnb uses AI to analyze listings and prioritize them in categories like "Cabins," "Amazing Views," or "Play."