How long does regret last?

[Jon Goehring]

I'm currently in search of my first real estate purchase in northern NJ. My girlfriend and I intend to use an FHA mortgage to buy a multifamily house. We have made around 10-15 offers so far and we actually had one offer accepted but the seller backed out after a month because he couldn't find a place to go. For all the other offers we have been outbid even when offering above asking price.

Obviously the market is really hot right now and some may even compare it to the market of 2006-07.

Im curious, for anyone who purchased a house around 2006-07 at the top of the market, do you still look back today and have any regret about buying at the top of that cycle? Do you think your investing career would’ve looked any better or worse today?

I know people on this site always say good investors buy in up markets and down markets but I’m thinking how much longer can this last? Do I just keep saving up money and wait? Maybe try to do a quick flip instead?