Now I haven't been in the STR game for long, but I do happen to have the largest portfolio of long term rentals in the Cleveland market so take this for what it's worth.....Some speculation based on some semi related experiences being the biggest name in the game in regards to LTR's.To me a lot of the problems you are encountering are a direct result of what type of property you're renting out.

Has anyone encountered this type of situation?

I wanted to get a handle on what recurring expenses I will be encountering there.

What is the process like, difficulties encountered, what to look for, role of an agent. 

What is the process like, difficulties encountered, what to look for, role of an agent.

I’ve had interesting encounters with realtors.

Has anyone encountered this situation before?

If my client asks to get access to measure and no matter how nicely I ask I encounter an uncooperative agent or seller I will explain the situation to my client other than just saying no.

It's like saying "I have this 100-club sticker on my car, and I have never had a problem with cops."

What’s been the toughest thing you’ve encountered when starting out at wholesale?