(to keep things simple)Property was primary residence for Person A from original purchase until 01/2020.

The book suggests some key metrics when analyzing deals and how the metrics should be to consider it is a good deal.

Turning a single-family into a multi-family is simple.

Simple...

Nowhere did or would I suggest that you self manage an STR. 

The strategies you mentioned above seem to be more advanced strategies, but if that is what you enjoy, learn as much as you can and get into it.With minimal income, I would suggest saving up some money, buying a new primary residence that you can house hack, and keeping your current property as a rental.

Trying to keep it as simple as possible, but cover the important stuff.  

This will make investing in midwest fairly simple.

However, if you’re unsure about future property values due to the unique nature of the property, this could pose more risk.What You May Not Be Considering:Financing Flexibility: Using a HELOC for repairs is a solid plan, but make sure the loan terms are favorable and the rates are manageable over time, especially with interest rates fluctuating.Vacancy and Maintenance Costs: Once all units are rented, factor in potential vacancy periods and ongoing maintenance costs, especially with multiple units.In conclusion, while the repairs are a big expense, the strong rental income potential suggests it could be a good deal if you manage the rehab costs well.

I've also known a few people who add  simple yard decorations or outdoor chairs to give the appearance of it being lived in.