I don’t like my tenants getting the idea that they will be charged anytime they report something wrong.That’s just my two cents without knowing the entire background on your relationship with the tenant.

The single biggest issue in my way currently is obtaining enough cash, whether it be my own, or through partnerships or family/friend-based lending (which I am very hesitant about to begin with as this could potentially strain relationships unnecessarily when money is involved).

Once you close and establish a relationship with them, I would notify them of a rent increase but we do small ones.

Building a relationship with local real estate attorneys or agents specializing in STRs in the area can save you headaches down the line. 

Since they are responsible for maintaining the relationship with you after the transaction closes, this approach adds an extra layer of confidence and security to your investment.If you can't find an investor agent that you like or trust that is also a Property Manager or works under a brokerage that has a Property Management Division, I would ask the agent if they recommend a Property Management Company.

I’ve also worked for a few investors, focusing on organizing maintenance, handling tenant relationships, and coordinating upgrades.Now, I’m venturing out on my own.

Would love to connect and get to know/meet investors on here and form a relationship where we can help each other.Thanks any advice is greatly appreciated!

That 36% rent increase while keeping happy tenants shows how smart and intentional you are about building relationships, not just cash flow. 

What I wrote above does not create an attorney/client relationship between us.

Initially, focus on building relationships with sellers rather than pushing for immediate deals.