It is a bigger deal, soil test, survey existing units, etc...multi year start to finish is my guess. 

Study interior photos if you can find them, that is the most valuable data out there.

You can use data from AirDnA.

This is a hard one to test, but referrals are big indicator.

I would like to find an easy SF home in my city and start small, test the waters on being a landlord, learn property management on a smaller scale with less risk, but I feel somewhat at ease because it is my hometown.

This means a whole different set of criteria, which in turn will dictate both the market and the strategy used to execute each step.I know ahead of time what that "list" will be since the plan is designed (and tested) before I push the start button, but exactly what that list is, I can't say...until I design the next plan.

Here is a quick map of the area:Let's get into some data, shall we?

This will help inform you of the value, but more data points always lead to more accurate data :) 

Some of the investors we work with have a lot of trouble as well with the owner portal and accessing ledger data.

Been checking out a number of data sources recently - some paid like neighborhoodcout and quantmaps.