The worst thing is to pay for a service where you don't get a benefit.If you have STR's and actively manage them, then there is a good chance that you can treat the propreties as active instead of passive which will allow you to offset the losses with other forms of income such as wages, interest, dividends, gains, etc.

Owning an asset is never a bad idea, especially if it's income producing.I would speak to a CPA about using cash from a WLI policy. 

There are houses that can be lived in and fixed up, or turned into multi-unit spaces (such as terraced houses with converted 'stables' at the back) for living in and earning income at the same time.

My approach balances both—ensuring that my investments generate income while also appreciating in value over time.

If debt concerns you, look at DSCR loans, which qualify based on rental income instead of personal finances.

It’s personal to the employees, who are directly impacted by the work culture of the business and rely on it as a source of income.

@Kyle LipkoRecommend you first figure out the property Class you want to invest in, THEN figure out the corresponding location to invest in.Property Class will typically dictate the Class of tenant you get, which greatly IMPACTS rental income stability and property maintenance/damage by tenants.If you apply Class A assumptions to a Class B or C purchase, your expectations won’t be met and it may be a financial disaster.If you buy/renovate a property in Class D area to Class A standards, what quality of tenant will you get?

For instance, knowing the income limits, family size requirements, and the types of properties that qualify can help you make more strategic decisions.

The home has a separate studio in the back for rental income with solid rental history but I am still trying to get a sense of the likelihood of consistency in renting it out as a short term or mid term rental. 

Especially in today's high interest rate environment, a low income buyer is usually going to be better off renting than buying.