Even on referrals a lot of contractors are hesitant to run around for investors new to an area until they trust that they will actually get work out of it.  

Park Hill Golf Course was owned by a trust, in the wayyy distant past it was previously a dairy farm, but it has been operated as a golf course since the 1930's!

Real estate is definitely a constant learning experience, and adaptability is key.Building connections with buyers in a new market can be a real challenge, especially when trying to understand their specific needs and earning their trust.

Having trusted resources in market have been helpful in managing our properties and contractors especially when my non-real estate related consulting business is in its busy season.

It's important to get to know your team and trust them before moving forward. 

If you don't trust your agent enough to tell you not to buy a house, then get a new agent!

@Warren Peasley you'll want to put it in a Trust.

Question 3: Is there a better way to protect property besides an LLC, such as a trust of some kind? 

If these continual expenses are not made  you end up with slum properties renting for a minimum weekly rate to transients.I don’t know your properties so I can’t form a specific opinion; however, based on the information you’ve shared I trust your opinion and knowledge.  

Similarly, looking up deeds of trust, licenses, or other public loan documents, as is often recommended here, will only confirm that the company exists - not that you are speaking to a legitimate representative.