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.

Wis Dells is a prime location for STRs to be eventually banned or very highly regulated given the large resorts with deep pockets and a lot of influence. 

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).

., 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?

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

Quote from @David Cianci: Quote from @Wale Lawal: @David CianciThe decision to create an LLC for your real estate investments involves various factors, and it's a choice that should align with your specific goals and risk tolerance.

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

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