I agree with your analysis methodology and does the same in looking at deals.

https://pinellashousing.com/calculation-methodology-and-pote...rental houses rent for around $2000-$2400 evn in C and B areas.  

Commercial MORTGAGE loan: larger than 4 units: Commercial loans typically use a DSCR methodology for their underwriting, so very similar. 

Important nuance here is that the DSCR Lender will qualify the rent based on the income for the property (i.e. the DSCR Metric) but the value will still be based on residential methodology (sales comps method, not income capitalization or cap rate approach)

Reach out if I can help, or you can find more investing insights, methodology, and processes in my (free) weekly blog: ericfernwood.substack.com...Eric

But then I dug into their methodology. 

I do understand that rental properties are a function of appreciation but wish to know what would be the best methodology to understand the overall negative cashflow to asset appreciation ratio or a metric to benchmark it against e.g. % appreciation YoY.

I would only ever recommend Guesty if you're a large PM using Trust Accounting methodology. 

I looked it over briefly, but it seems to be pretty detailed on their methodology and includes really helpful tips in the front pages.

I have used three different analysis methodologies for determining the right price to pay for this property.