Despite higher interest rates for the mortgage (7.625%) and the HELOC (9.5%), we are still positive cash flow.

Don't wait too long, because those gain may lose value based on time, trends, or rates.

Specifically, do you look at comps on the market or try to find what value would be based on the cap rate? 

I clicked on the link and their starting interest rate is 11.1%.

I basically wanna know the rental occupancy rate in that area.  

This will continue to push up the prices.Sales - Months of SupplySales - Median $/SF by MonthDespite persistently high interest rates, the $/SF continued to climb.

Every time I inquired about commercial loans on my SFR I got quoted much higher rates and loans that were amortized over 30 years but always callable every 5-10 years.

I also have a primary residence with nearly a JUMBO loan at a high interest rate and I own a vacation place in cash (small trailer not worth much money but i also own the land) in a different state that I pay RE taxes on. 

I don't think I would advise anyone do something or not do something because it might be a "red flag" - yes the IRS has plenty of red flags, but the audit rate on most of these issues is so comically low, that as long as you have a legitimate position - take it, don't not do it just because it might slightly increase your chances of an audit. 

The duplex was expensive and with rates as high as they are, I was not able to save money house hacking.