Between third and fourth and then fourth and fifth, did you not consider renting as a sort of try before you buy - to see whether the location worked or not?
Never considered renting as we had long ago entered into the home ownership world and hadn't thought of ever going back to renting - I wasn't an investor back then with the knowledge we all have here. We were happy with our location picks every time.
When we sold our 3rd PPoR (B&B property) we made enough of a cap gain to buy our 4th PPoR outright. It was lucky; we bought in an area that was about to take off and we didn't know it would, and our next house was in an area which was a fair bit cheaper by comparison.
But then again; we mortgaged ourselves up to the eyebrows to buy no.3 - it was for a B&B venture we wanted to do. We backed ourselves and took the plunge; that's making your own luck.
We spent a year renovating it (spare time, weekends etc). It did ok, but the dollars in B&B's is not that flash, and we ended up having to work full-time and try to fit in the B&B as well. It got too hard and we never had any money to play with. Sold up and bought down by the beach in no.4 (across the road from where we now live).
While in no.4, we got offered the block across the road which was owned by our neighbor; they wanted to sell it, they knew we were interested (better views and on the low side of the road with the views behind the house - better privacy), he offered us a good deal and very long settlement, so we bought it.
About this time, we decided to move to the USA for 3 years so my wife could do a work contract. We rented out no.4, and we were renting so to speak while in the US.
We moved back and rented a further 3 years while I renovated no.4, sold it and built no.5.
Secondly, why keep building - this is a costly exercise - with established houses you get a lot of extras built in e.g. landscaping, fencing, etc
True, but PPoR no.2 was a very cheap block I found near work when I had some cash saved. I bought it for cash with no loan. It was simply an opportunity at that time.
With the current one; we knew the potential of the block (next door to the owner of it and they have unbelievable views) and always thought it would be good to have it. It got put in our lap pretty much, so we had to do it.
I think that PPORs are like wives and cars. You should not keep changing them all the time as they are extremely costly to maintain.
Churning wives is about the most expensive thing you could do I'd say.