I am not yet familiar with the management fees for an STR yet as we self manage, however Cleveland itself is currently STR friendly and just requires them to be registered if you have stays over 90 days and then you register with the city and pay $35.

.- They can rent by the room and self-manage to produce day 1 cash flow.- Many of these HCOL areas also have strict limitations on AirBnB or short-term rentals... that do not apply to owner-occupants - thus allowing for extreme cashflow potential for house-hackers.

Remember, the notion of amassing wealth without investing is a dangerous myth perpetuated by self-proclaimed experts.

I agree that the best way to make money is self manage your short term rental (not AirBNB, that is a platform).

We want to plan in the most tax vantaged ways (which includes keeping future AGI as low as possible) and open to new-age and creative concepts.Respectfully ask to keep discussion to topic vs. selling one's self or services seeking new business.

Start with books and self-education before considering any paid courses!

My former journalist self enjoys digging into Colorado laws and counseling my clients on where they can do short-term rentals and under what circumstances.

In neighborhood it is very important to present your self to the home owner next to you, this helps a lot to prevent misunderstandings. also this shows your professionalism.

We own over 100 units in San Diego and have always self-managed. 

We are both self employed so retirement is something we have both started thinking about.