If they're in the same state, that will make your legal team more streamlined, but otherwise, you have to form all new vendor teams when assets are scattered across multiple MSAs & states.

I had a few tenants e-sign 6 documents with multiple pages in a couple minutes and realized they did not read any of it! 

Quote from @Cameron Porter: I’m already an agent new in the game.

Take that and use a 3-5x multiple and then you have a better idea of its worth. 

A disadvantage to this type of investment is that it's likely your MOIC (Multiple of Invested Capital) will be lower than that of a common equity investment. 

I've found the same when using pricing tools, but I've heard from others that it's been a game changer for their business...

I figure the upside to the rental scenario is, of course, investing in multiple properties, while a downside would be having to most likely get a conventional loan on the second house with 20+% down and proof of sufficient enough financial reserves to handle two mortgages. 

I have the opportunity to list sell multiple acres of virgin waterfront property in Trinidad and Tobago.So I'm looking for potential investors as well.Which islands do your company typically operate?

I currently house hack in Chicago, however, going from that to STRs where I cannot self manage is a different ball game and just wanting to pick peoples brains who are doing what I'm interested in doing.  

For brokers, it is a numbers game and most of them want to consistently bring on new agents.You may have to meet with multiple brokers to decide which is the best fit for you.All the best!