However, as the owner you still need to spend more than 50% of personal services and more than 750 hours on the real estate business on your own.Alternatively, short-term rentals are generally treated as active business income and therefore are eligible to offset w-2 income.Navigating the Real Estate Professional Rules"When measuring material participation, a married taxpayer is required to count any hours performed by his or her spouse, even if the spouse does not own an interest in the business or if no joint return is filed.32 While this rule is advantageous because it makes it more likely the taxpayer materially participates in the real property trade or business, it is a trap for the unwary in the real estate professional context, as discussed below in Step 3.""

I'll be taking measurements to see what is feasible.

The 1% rule is also a useful measure in my mind for an initial screening.

Begin modestly, take measured chances, and absorb failures as well as victories.

The second property will be purchased with a mortgage (you can determine how high or low the leverage will be by adjusting the proceeds you use or the price point of the 2nd replacement).You are adding some measured debt at a level that your dad can be comfortable with. 

Beyond the fact you are new to the industry will be tying up your investment dollars for multiple years before you start to see any measurable ROI. 

Other public forecasting apps only available up to 6 months.For the second software , it analyzes the contractor/BRRS activity in many metro thru MLS listing and measures the ARV based on previous condition sale and after selling ARV.It will tell which house has the most potential.I will tell you all over if you want to rehab, do it in appreciating markets like CA, WA or CO.

Not sure if I will spend more money trying to get that back via legal measures or not.   

The important measurements are annual earnings and net worth.

But if it is turnkey, I am assuming you will probably not be ahead on cash flow from your current property (and likely less).But I want to reiterate, if you say you are an investor and your focus is scale and number of doors, you are measuring the wrong metric.