I would compare my return with any market, anywhere but 1) this is a different San Diego market than the one I have been so successful in 2) while I am a big fan of leverage, I am not a fan of over leverage.

Property Valuation:Investors look at a variety of factors to determine a property’s value, including comparable sales (comps), rental income potential, and location.

Financial Projections: Compare the projected monthly cash flow from renting (especially with an ADU) to the net profit from selling after costs.

There are plenty of deals in Philly on and off-market from wholesalers, who are pretty decent in Philly compared to other places.You will need to get your GC license here and learn the permitting process and necessity here as well.

However, comparing the rent of the investment property to your primary residence mortgage isn’t the best measure.

The thing I didn't like about RentRedi after doing lots of research and preparing a spreadsheet with features and costs, is that RentRedi doesn't disclose up front that the accounting portion is linked to another company and is extra and, frankly, comparable to the pricing of the "big boys."   

A property doesnt increase in value just because an STR is run successfully on it. its value on paper is based on the comparables in the area.

I'm not saying you're doing this, but people will often make the mistake of looking into the highest priced rental unit and making that the "market rate" but it's often not a true comparable to the subject.

It’s worth calculating the total investment (purchase price + wiring replacement) and comparing it to what the property could yield after the upgrade.

Comparable property sales do not affect the depreciation basis, which is determined by actual purchase and improvement costs.