I'm also relatively young and interested in some more "challenging" investments (although recognizing that I would have to do everything remotely and source through a property management company like yours).

A 12-month policy was only ~$900

Has anyone every worked with or heard anything about a company named Five Stream Ventures? 

I  took over a mature company that had an investor base that I think average age had to be 65 to 70..

With our structure, the development company owns about 45% of the equity when complete, and I own 50% of our company.So it will be about 22%

I’ve heard about partnering with insurance companies for displaced families, working with military personnel in need of temporary housing, and possibly connecting with other organizations that require mid-term accommodations.I tried reaching out to GEICO about insurance-related housing needs, but they didn’t seem to have a clear process.Does anyone have experience with this niche?

I own an HOA management company in Hoboken and it's led me down this thinking-path as well.

Doesn't that help keep property taxes lower or the owner-occupants.If 5% of the properties are being bought by investment companies, that means 95% are not. 

I will note though that lots of people manage multiple rentals without hiring a STR management company (myself included).

Those companies you asked about are more for deal finding and direct contact to off-market sellers, is that what you are looking for?