I didn’t see your location in your profile or your post, but assume at least 17% state/federal taxes leaves you with $10k/yr. 

@Ana Vhan there are many commercial options where you can add multiple locations/multiple states onto a single policy.  

I’ve realized I need additional help—someone local, like an assistant.Here’s my idea: I was thinking of purchasing a small piece of property and putting something modest on it, like a single-wide home or a similar small structure.

Local relationships with INVESTORS and SYNDICATORS. 

Quote from @Clayton Silva: Quote from @Jeffrey Blackman: Quote from @Clayton Silva: 2nd position HELOCS on investment properties are typically capped at 70% LTV and have rates ranging from 9-11% just a heads up unless you use a local credit union where you have cash on deposit with them. 

If you owned the local grocery story, you wouldn't apply their grocery bill to their rent payment.

Just, "that's the next cave" over.I joke because you live in the best of times to locate properties, all we had were cars and feet, to drive neighborhoods and locate deals.

I am considering getting into this space (looking at some courses), but worried that its too late, and that deep local market knowledge/understanding of buyers/connection with developers etc is required to make this work, which only incumbent/long term investors will have and would be hard for a new entrant starting from scratch to catch-up...is my hypothesis valid in your opinion ?

Hello,I am currently located in Dresden Germany working for Infineon.

Keeping your STR local would be the best case.