So I'm on Schedule C .... and my very expensive home ultimately generates a large loss.

However, the current vacancy is hurting your cash flow, the paused refinance poses challenges, and ongoing capital expenditures can be significant.Short Term Rentals: These can generate higher monthly income and offer flexibility to adjust rental rates based on market demand.

The more bedrooms per unit, the more unit you will be able to generate.

Similar green energy investments could be considered if you can make the numbers work (credits on some types of low income housing can be north of 50%).Depending on how long these properties have been held, they could consider implementing cost segregation studies via a change in accounting method to accelerate some depreciation.The operating proceeds could be re-deployed into new properties where cost segregation is an option to accelerate depreciation to offset proceeds.If the properties are low basis and we are not maximizing the 199A deduction, maybe considering an S-Corp structure for management to be able to participate in retirement plans and also generate wages to use as a 199A base. 

We were initially looking to flip homes, which would potentially bring higher immediate cash returns for her enjoyment in her later years, however I’ve been researching the brrrr method as well to generate cash flow without the stress that flip process may cause her.

As long as you have reliable "boots on the ground" such as a property manager or real estate agent that has experience working with out of state investors, you'll significantly increase your chances of acquiring the right property that will generate the returns you're looking for. 

Many of those on it seem happy to remain on it cradle to grave generation after generation.1% (approximately) are in prison or in the court system on their way to prison. the gray bar motel.42% Are suffering from going through the divorce court system.

Confused because DSCR by nature looks at the income the property is generating and not your personal income or credit I believe. 

To be clear, I'm thinking I would do the above for several years while building my portfolio and learning, and then solely focus on my portfolio once I'm established and am generating enough income to live off of.

We actually rented the unit back to the existing tenants for as long as they wanted to stay because we didn’t have to do anything to the unit to start generating income.