I rent it out as a vacation home to others too... this helps pay the bills.

(I also do all of the advertising, tours/viewings, communications resulting from the advertising, but once all of the rooms are rented, and I am purely managing, how are property managing hours discerned, I suppose that's my question here.)

But in a year you could move back in with your parents and rent out both sides of the duplex… just a thought for you.  

 I think changing from a “don’t rock the boat, keep rents stable for ‘good tenants’ ” mindset to a Vacancies aren’t the worst thing on the planet mindset as paid off in spades.

The condo will have monthly association fees that will significantly eat into your bottom line once you move and rent it out.

(with conservative assumptions on annual appreciation - 2%, and annual rent increase - 1%, as well as 5% vacancy/maintenance).I see so many people say they only go for properties with at least 15% cash on cash returns, which seems extremely difficult in this market

There is also a house on my farm that I want to renovate, rent, and refinance. 

My wife and I have been buying, flipping and renting for 15 years.  

I would say First and last month's rent, plus a matching security deposit that is equal to the rent.  

(renting out by room would net me better cashflow).