Is your plan to retire with portfolio that will sustain your lifestyle by a certain age, then your answer will be to reinvest and purchase more properties. if you like your job and not in a rush to leave, then you can pay down principal.

I've ran some preliminary numbers and it seems sustainable but I would like more information from people who have experience doing it.I would love to hear any stories or advise on anyone who has had experience renting out their vacation home. 

@James Wise, I suppose if you are cash flowing well enough to begin with on any prop, you can sustain pulling this unexpected addt'l annual expense off your bottom line numbers without it hurting  you too much.  

I was a thrill chaser and wanted a fast buck but learned "slow is smooth and smooth is fast" and sustaining a progressive upward trend was more valuable and repeatable.

My plan was to switch industries, because I am unfulfilled at my current employer/industry and I wanted to get into selling large scale solar projects to large apartment complexes and businesses because I have a strong interest in sustainability/renewable industry.

I was supposed to build sustainable homes and sell them (which i plan to revamp that strategy in the long run, im not giving up on it) now i am into buy and hold investing.

After being able to gain first hand experience and establishing relationships with the proper parties, I would then like to move back knowing that i have created a solid foundation in that region/ market that would allow it to be as self- sustainable as possible.

The scenario typically plays out as follows:We report to the lender what we are earning for rent (and provide leases when requested); The lender usually says the amount we are earning is over market and not sustainable;They then attribute market rent to each unit of the house and include that amount at 50% - 70% depending on their inclusion rate.The first time it happened, I try to make the case for including the actual rent and the lender countered that they could attribute market rent or strike the property's income (but not its debt) from their calculations.Now, Canadian lenders are traditionally more conservative in their underwriting practices than those in the U.S.A., so you may be fine getting a lender to consider your actual rent on the property. 

Thus, I doubt anyone can create a sustainable business model that involves charging $500 an hour with a final bill ending up in the $1,500 to $2,000.

I know things are probably exciting and new now but keep in mind that you’ll need more than attraction and hobbies in common to sustain the marriage long term.