I’m in no rush to move once I get into something, especially if it makes more sense to stay out for an additional year or so.

Not saying it can't work... just requires additional caution.  

Yup more monthly fees.. 

It’s not so much a cap but by the time lenders add in all there fees, origination fees, doc fees, etc it ends up feeling like a 20% down payment to close instead of 10%.

Then add in all the fees that are being added by AirBnB, VRBO, etc. and hotels are in many cases a better deal . . . less surprise fees and fewer owners that have odd rules. 

You can pay a membership fee or $20 at the door to get in.

Aim to purchase and renovate a property for resale, with the ultimate goal of acquiring additional income-generating rentals.

As OP said, hard to find umbrella that will cover STR papered insurance unless I find a carrier that writes it under my name personally and names the LLC as an additional insured (I own my properties under LLCs).  

@Wendy Pattonyes, thank you for the additional information. 

Perhaps the cable company charges a small fee and can do it themselves?