I know people can't predict the future, so what would you recommend based on the last 10 years.Also looking for suggestions on commercial brokers in both markets.Thanks in advance, best of success! 

You have made some pretty accurate predictions!  

Essentially that phrase is saying that real estate investing is pretty predictable once you get your head wrapped around it.

Can you predict that?  

Since you inquired, I'd rather not disclose my income here, though it is steady and predictable.  

The same happened in 2013 and 2014, but once again - prices didn't go down.If I decide to invest now I won't have many neighborhoods to invest in and my returns will be low, but im afraid that if I keep waiting and prices will keep going up I won't even have that option.I just can't predict if prices will go up or down soon.

The City is doing a lot over the next couple years to better that area and in 5-10 years, I predict something like a triple in investments there, but as far as living there now, and with a family, that's entirely up to you.

As for the bank, I can't predict if they are going to agree with that much seller financing.

Now, predictably this guy is now trying to reach out to me asking me for different issues dealing with this 5-unit (closing, managing once it closes, etc...).

No one can predict costs and values that close and small variations will kill you.