It's not "our" conversation and I personally love your insights, whether I agree with them or not.You know I think you've created your own mix of lifestyle/investment purchase.

Some people just don't have good mentors in there life, and/or need to learn through mistake.

You can still find some great cottage style homes or even 2-4 units close to the beach that have great STR returns.One good thing about being out of state in IL is you can find a good Single family home, Condo, or Townhome and call it a Vacation home and only need 10% down. 

At the end of the day, that is life however to Stuart's point, you may want to consider investing in better areas where this does not occur normally if this is an unsettling occurance for you. 

It creates a lot of friction with other tenants and normally creates a poor work life balance for the manager.

Any recommendations for institutions that can extend a line of credit backed by a whole life policy?  

Ask anyone with investment property and they'll tell you it's not passive.I earn enough from investments that I could be financially free for life, assuming nothing major happens.

Here's the details:I was listening to a BP podcast or BP adjacent podcast over the last 2 weeks and I remember it mentioning a company that can assist in styling for renovating homes. 

A set of new machines can easily run you 300-400k if these are all end of life.

Don't make your life more complicated than it has to be.