In my mind, the liability and possibility of harming the seller outweigh the rewards.  

It was 20% down  Like I mentioned on my comment above, it is possible to still finance this property with a non-traditional lender, especially when you are putting 20% down.

The Lake Tahoe market has many intricacies regarding short-term rentals, but navigating them is definitely possible.

-repeat the process every year by acquiring one house every year with the appropriate income qualificationThere are several ways to run and make sure you are maximizing your rental income while keeping your living expense as low as possible.

Therefore, I don't have definite plans for how long I'll stay in Oregon, and consider the possibility of someday returning to the Austin area.

I know curb appeal is important, but is it possible to overdo it OR even have no curb appeal at all?

Only allow inspections after the contract is signed and locked in (if possible).Ultimately, gauge the buyer's credibility—are they responsive, experienced, and able to close?

I will be talking to him Monday, or possibly today if I find time at work.

My research said it was possible to use my RE Agent commission towards the down payment but he said we cannot and I just let it go.

Part of the investment thesis was getting it for a bargain, then building an ADU complex on it as affordably as possible, getting it to cash flow, and realizing value on both the rental income but also property appreciation given the work going into it.If the property will really only be worth ~$1.70M once we are finished, I will likely just stop the project now and exit the house as soon as possible.If you do not get dollar for dollar for projects such as this, how would house flipping ever work?