In the area where I am specifically looking (Chester County), I've been looking at the historical data for renter-occupied vs owner-occupied and the numbers have slowly risen - to me this is a good sign of an area I believe I should be looking for as I start this journey.

I do not know the metrics for the area, but if the population is growing, jobs are diverse, historically RE appreciates faster than CPI, you indicated nice area, this may qualify as a single.  

I’m in San Diego, housing price is historically high, I was so attempted to move the investment  to a better school district, but of course property tax and everything else will be more expensive too ..  

If you are using appraisal with plan for commercial use they may be able to factor historical information, but I would doubt they'd have the experience or speculation to factor what potential short term rental income could be.

Having 5 or 6 months of supply is historically average — at the end of July 2021, Chilliwack’s months of inventory was just 1.9.Large numbers of residents are moving out to Chilliwack from closer to the Vancouver core, especially as work-from-home options remain in place by many employers.

The home is an old Victorian style house in a historic part of town, but I was planning on doing a home inspection and appraisal to determine how much it should go for.I'm still new and feeling my way in this and wanted to know if anyone could recommend any particular strategy or if you knew any agents that you could recommend that would be successful.

You're in Charleston - one of the nicest cities in the country and full of historical charm. 

I don't expect to see a significant drop in prices especially with historically low interest rates.

A worldwide pandemic, social distancing, facemasks, a recession, historic unemployment, evictions, foreclosures, record-setting heat, power blackouts, Black Lives Matter, and a level of social unrest perhaps never seen before, have all changed the way we live and treat each other.

My co-worker that's under contract to purchase a historic home built in the 1890.