Continue to scale my personal RE investments and learn!

i think you can be successful if you are willing to do what you alluded to, which is spend time in person in your chosen market. 

I want to exit as I don't get any personal use from the STR being 20 mins from home and would rather apply the capital to another opportunity in multifamily (LTR) or another STR in Hawaii where my brother is a broker and now manages STRs.

Be sure to actually contact the landlord for verification—fake references are more common than you’d think.In-Person Meeting: Meeting potential roommates in person is a great way to get a feel for compatibility.

This is advantageous bc later you have a third party loan (not your personal money) so seasoning period is 90 days to DSCR out. 

If you are just a plain person they usually must serve you in person. 

Personally I would want to manage the rental myself at least in the beginning to make sure you get good ratings.

I personally feel landlording in Indianapolis is pretty easy as far as restrictions go.  

However, he asked me to sign a one-year Exclusive Right to Represent agreement, as presented to him by his brokerage.His interpretation is that it applies only when he materially assists me, but I think the boilerplate brokerage language he was given reads much more broadly:"If during the term of this Agreement Buyer enters into a contract for the purchase of Property through the services or efforts of the Broker or Buyer’s Brokerage Firm, or by or through any other persons during the term of this Agreement" (emphasis mine).My concern is that, under my interpretation, if a fellow real estate investor wants to unload a property or if I get pointed to an opportunity by a former agent, colleague, or friend, this agreement could create an obstacle to moving forward with the deal.In the end, I didn’t sign.

Signing the lease demonstrates they agree to the terms and then you can hold them accountable.If you don't do this, then the person named on the lease and paying the rent could disappear and you would have no legal authority to charge the remaining three for unpaid rent.