Your advice will be invaluable in helping me navigate these initial steps and lay a solid foundation for my future in real estate investing.Thank you so much for taking the time to read my post and for any guidance you can provide!

Anyone who instead attempts to buy me Coffee so they can sit down and "Pick My Brain" is immediately placed on the "I hate this MF list."

I currently have one property listed on Airbnb.

Utilize online platforms, real e­state listings, and work with local real estate­ agents to search for potential prope­rties.

I considered SFH where I'd rent out all the rooms and keep one to myself, but this seems risky since I'll realistically be away for months at a time and couldn't manage the unit/other tenants.Then I came across some listings that appear to be hotel rooms for sale, with basically the facilities I need (a bed, toilet, kitchen), a price point I can handle (270-500k$, I'd do 20% down), and fairly high HOAs (~1500$/m?).

I’ll make sure to add the other two to my list.

Does this mean there is no downside to listing it for the maximum price of $4313 per month since the tenant would likely be paying the same amount no matter where they chose to live?

If you're unable or don't want to list them as an STR. 

I'm looking for opinions on flat fee listing services.

They will have lists of people that have been looking at THEIR rentals and may be willing to help advertise yours for a fee (assuming you want to manage it yourself).