I left 2 years after purchasing however I have had numerous property managers that miss a lot of things that I had questions about and you would be surprised how I catch things at times. 

No more multiple log ins and keeping track of numerous websites for PMS, pricing, cleaners, team operations etc.  

short answer: there isn't one.there are numerous moderate and high risk ways. 

I have found numerous properties that cash flow but I need to do a lot more research on the cities itself.  

There are numerous lenders on the site that should be able to tell you what's available.

Thank you for taking the time to answer and for providing the numerous resources, I'll definitely take a look at these.

My initial understanding suggests that Short-Term Rentals (STR) might be the appropriate route for me, however, my knowledge on this is quite rudimentary and I have numerous questions I need to address before making a decision.

There are numerous advantages to this strategy:-Learn the basics of managing a tenant and property.

There are numerous examples of HCOL investors like yourself who bought 1 or 2 or 3 and got crushed because they weren't ready for the CapEx on the old, creaky midwest housing stock; didn't have the right team; didn't do an inspection; etc. 

This site is an incredible platform that has numerous resources so definitely take advantage of it all.