Not sure if you plan on pursuing a higher education, but that can be a factor that comes into play as well.

The most important factor is consistency, as jumping from one strategy to another over a short period is ineffective.

There are other considerations that may still make it impossible to permit the construction of the building even  if the by-right use permit is obtained and its important to have an architect closely examine how the proposed floor plans will layout to confirm egress &  bedroom windows + localized zoning overlays along with a  number of other factors.

However, when you factor in the HELOC, we have a negative / break-even cash flow (HELOC payments are about 25% of the revenue from both).

You'll be buying in a specific location, subject to local rental regulations and other unique factors.

., including floods, earthquakes, and severe storms.USDA Wildfire Risk to Communities – Offers detailed insights into wildfire risks for homes in specific regions, particularly useful for properties near forests or dry areas.Risk Factor – Analyzes flood, fire, and other climate-related threats for individual properties, giving you a risk score.Climate Check – Delivers property-specific climate risk ratings, covering heat, drought, fire, and floods.Do you consider environmental factors like flood and heat when investing?

Most focus solely on due on sale clause as the deciding factor. 

See the chart from Fair Isaac Company (FICO) below: FICO Score Pct of Population Default Probability 800 or more 13.00% 1.00% 750-799 27.00% 1.00% 700-749 18.00% 4.40% 650-699 15.00% 8.90% 600-649 12.00% 15.80% 550-599 8.00% 22.50% 500-549 5.00% 28.40% Less than 499 2.00% 41.00% Source: Fair Isaac CompanyAccording to this chart, investors should use corresponding vacancy+tenant-nonperformance factors of approximately 5% for Class A rentals, 10% for Class B and 20% for Class C.To address Class C payment challenges, many industry "experts" are now selling programs to newbie investors about how Section 8 tenants are the cure.

What factors do you think I should consider to determine if it makes sense?

And of course they are paid to go pick up materials, or that is factored into their bid.It all comes down to communication between you and your contractor/handyman.As an investor buddy of mine says, I don't let anyone else spend my money.