It is true that every step taken in life is, for the most part, a calculated risk, and we all want to come out ahead while using our wit to benefit ourselves and our families.

Factor in tax benefits.  

Now the numbers don't work.I went back to the drawing board and decided I would benefit more if I used the majority of the funds on the cottage and add a bedroom addition, while keeping the caterer in place and collecting higher rent.

One of the tax benefits of a rental is the noncash depreciation deduction that serves to shelter cash flow from tax.

A benefit of a 1-year lease is that you know you won't have a vacancy for a year.

No SSAE16-Soc II report on file, No E&O, no regulatory body governing them, no audited financials, no policies and procedures on NPPI data, etc.) they aren't going to be able to call an institutional lender/servicer/bank to buy a note.Our diatribe ends up being to the benefit of the OP.

@Pari Rizwan I don't have a clue as to what your goals in the real estate industry are so I would have no way of knowing if a sales agent license would be of a benefit to you.

Could be that it's a lot easier to fill a 3/2.Almost every month there is some small repair needed (e.g. plumbing).The benefit of being in the area is that I could meet with the property manager in person and build a way better connection like that.

Over the years I have always been bringing it up to my wife how much of a benefit house hacking would be for us financially down the road. 

Flipping sounds sexy, but its a job more than it is investing and you don't reap the tax benefits of owning real estate long term doing that.