There was a barbecue pit in the back yard with the remains of a trash fire in it, milk crates for lawn furniture, piles of beer bottles, and the remains of a camper that someone was living in.

Sorry Roy, We in Toronto had milked all we could out of this cow, we are kliing eachother for a peace of 100 year old property selling for 700K that needs a total gut and 100K of renos and paying 150K over asking price, competing with 10 other people on the same property.But think about the positive side of it, we are going to start buying where you live and your properties are going to appreciate like never before because of the competition, free money without working, isn't that nice?

Money Mustache's blog (I'm a big fan).

Most simple thing, do math for both hypothetical situations and see which one brings you more money, consider rent you will pay, and the interest you will pay for heloc for cash out, and whether you can finance the new properties or not.I personally would never sell a SFR in an appreciating location so I can milk it during every cycle.

If the appraiser thinks/states they will violate USPAP by providing a limited valuation and tells you they can only do a "full" appraisal or the like, they don't know what they're doing or are just trying to milk your money.

Some professional tenants will pay the rent on time but then milk the landlord for free utilities.

Money Mustache, (financial independence blog) and while reading that site, I saw an advertisement for Bigger Pockets, clicked on this and instantly got the bug.  

Vehicles depreciate but sometimes you can milk some low interest money and value out of them to put into lucrative endeavors if timed right, and not wasted on unnecessary things, haha.

Regarding contractors, they seem to have a shelf life - like bread and milk - none that I'd be confident to recommend.Try HomeAdvisor 

You never want to be 100% occupied because that's like being a convenience store with no bread or milk.