So one Primary, one Investment and one Vacation/Second home.

You just have to make sure once you vacate your primary and converting into a rental, how would your DTI (debt to income ratio) be effected.

I've spent so much in inspection fees and sewer line scopes with offers OOS, could have taken my kids on a nice vacation with that money.

They indulged in luxurious residences, high-end vehicles, and extravagant vacations, all while their investors faced mounting financial losses.

His lease isn’t over till the end of Oct and clearly states that “If tenant vacates the premises before the date agreed upon in the lease, the tenant will forfeit deposit and will be responsible for rent until the end of the lease.”

The biggest reward of owning and managing vacation rentals is much greater than financial; the friendships I have made with people around the country are priceless.  

And first, examine where you want to vacation first. 

Any way  so in a short hand way I agree with you on stopping to smell the roses when your young enough to do it.. but many simply dont have those choices they choose a job that they must keep at until they can retire and maybe  a week vacation to Hawaii or go party at Vegas is some highlights. 

List the property as soon as you can so hopefully it doesn't stay vacant for long.I'm slightly bias because I recently moved in to a new place and vacated my old apartment with still about 3 months left on the lease.

@Alan Asriants and I left out expenses like 10% for repairs at 5% for vacancies because I am so skilled at this I have never had a place vacate for less than one week because I keep them ship shape so it moves out.