Nonetheless, corrections do happen in markets eventually and can deal out some serious pain, he says.
As a result, every home owner, buyer or investor, needs to consider their personal vulnerabilities.
Can you get another job if you lose one, or will you hobble to age 65 like Bolton's father did thanks to the fallout from the 1987 stock market crash?
An important lesson from the 1930s depression is that when the market went into freefall, there were no investors left capable of buying.
That means that property owners who think that their property is like cash in the bank or that it's their emergency fund could be cruelly mistaken.
Thanks to the RBNZ loan to value ratio (LVR) restrictions there is a lack of liquidity in the property market, says Bolton.
What that means is that the LVR restrictions have reduced the number of buyers in the market who aren't buying at the same rate as before. The harder property becomes to sell, the more "illiquid" it is.
With an eventual correction inevitable, because all markets correct eventually, and a lack of liquidity through LVR restrictions, anyone with a foot in the property market or planning to buy really needs to be careful.
"I said after the RBNZ put 60 per cent restrictions on borrowing (restricted investors from borrowing more than 40 per cent on properties) no-one was appreciating how much liquidity they were going to take out of the market."
Bolton adds that even if we aren't currently experiencing a "big market correction" that doesn't take away the fact that the lack of liquidity in the market makes life riskier for homeowners.
He cites a number of examples where property owners have come a cropper of late. Often it's due to making assumptions. One business owning client decided to buy himself a commercial property and went unconditional before organising finance.
"He presumed the bank would be sweet, which it wasn't."
In another case an investor client was selling one property to free up capital for other purposes.
To his horror the bank took the proceeds and used it to pay down his other loans. The fine print in banks' mortgage contracts mean they can and sometimes do, do this.
Several others have bought property assuming the bank would say 'yes'. "The bank said 'no'."
Another big issue for homeowners in particular is that many live beyond their means and roll their credit card debt into the mortgage.
That's fine when property values are rising. But when values are stagnant it might be difficult to get the bank to agree to extend the loan, which can prove problematic.
Being conservative in today's market, says Bolton, means being sure you can genuinely afford the property. Being conservative is also not buying until you've sold.
"There is this assumption you can buy and just sell your house," says Bolton.
"That has clearly changed. You could buy (in this market) and find you struggle to sell for the price you thought you could get. Be realistic and just move on."
Bolton says when seeing mortgages for clients in this situation it's best to be conservative.
"They say my house is worth $1.3m. I say I will get approval based on $1.1m."
Investors also need to be conservative.
"Banks are far less tolerant of investors than they are of homeowners. They don't want to kick people out of the family home. They will move pretty fast if you are an investor."
He recommends investors split their investment properties between banks so that like the investor above - who had his cash snatched - the properties are not cross collateralised.
He also recommends keeping one property totally separate and not too highly geared so that if they need money in a hurry they can borrow against that property.
"I call this a cash bullet," he says.
The other thing he tells investors is to have a decent chunk of available capital on revolving credit to cover any short-term crises.
Finally, he says be proactive if problems arise. The worst thing you can do is stick your head in the sand.
