Specialty Leasing of Condos

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Does anyone here have experience with owning executive or corporate lease on condos? How about leasing to students? My area has a lot of travelling business people as well as a small local college with no on-campus housing.

I am looking to invest some money I have sitting in a self-directed 401k and by my calcs I can afford two 2 bedroom condos in my community. My theory is if I furnish the unit, I can rent for short-term at higher rates thus create greater cash-flow.

I have read many pros and cons about investing in condos and I get it. An unexpected assessment, high HOA fees, the neighbor's pest problems, and so on; I am just researching specialty leasing, if I can call it that.

Has anyone had success or failures with this approach they don’t mind sharing?

Is there a rule of thumb calculation to analyze the feasibility of this type of business model?

Does my theory above hold any water?

Thanks in advance for any responses I might receive.