What David indicated is true where my rentals are located. 

@David Cruice , in the process of buying the property, the OPRA docs indicated that the septic system hadn't been replaced in the prior 60ish years and was rated for 3 bedrooms (not 6 that come with the property).

@jeff khel thanks for your input, I ended up retracting the contract as the homeowner had all these additional stipulations indicating she wasnt as motivated as she claimed she was.

But, if you drive around the city, especially downtown, new construction is happening all over, indicating that the city may just be in the beginning of a rise.What are you thoughts?

At any rate I will leave a sign on the front door indicating your intention  and schedule.

What indicator(s) would you recommend looking out for to know when the "right" time to buy is?

Your agent needs to get the listing agent to indicate where you need to be at in order to make the deal happen.

My research indicates I'd probably be looking at an interest rate between 8 and 12%; is this true?

Both the Vanguard and the Schwab indices are great!

But if you only look at the data that caused the last crash as an indicator for the next one, it will blind side you.