Hi Max, being "caring" and having a conversation with them at the door can save you.  

You're feeding 2 dogs with one biscuit by taking care of your living expenses and generating rental income at the same time, and by living in the house and keeping it to 4, you generally get exemptions on things that might bother you to live with (IE you can choose whomever you want as your tenants without running afoul of fair housing laws).

VA Loan Did you work with any real estate professionals (agents, lenders, etc.) that you'd recommend to others?

And do they care if I do rent by the room strategies?

Best of luck, but again, I suggest hiring a professional. 

Real Estate Professional = 750 hours and more time on real estate than anything else.

Who will drive by to see if the lawn is cared for, or if there are three unauthorized dogs in the back yard?

(One went with another manager eventually, and the property is listed for $400/month less than we listed it, and the other finally got rented to a solo professional.)

Budget carefully, prioritize high-ROI renovations, and adhere to strict timelines to maximize profitability.

I could care less if anyone used my services.. we do just fine without one off beginners.