You could even consider a condo with an established HOA that’s STR-friendly—it can simplify maintenance and management.A Few Other Things to Note: Documentation is everything.

I think one of the biggest analysis paralysis thoughts is on landlord- or tenant-friendly areas.

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Hello investors and passionate property owners! I just wanted to reach out to introduce myself. My name is Paul Hearn, and I am a new real estate agent in the Memphis area with a burning desire to work with investors ...

Quote from @Gregory Schwartz: I have 2 very close friends who grew well beyond 2 rentals with this strategy. 

(You won't make any friends. 

I did a "blind" assessment where I paid/reimbursed a close family friend to go in as a guest because there were a lot of details I wasn't privy to- and wanted to understand (the whole experience and process from the guest perspective from the initial inquiry, emails, etc.).They shared the email communications (some of which was glitchy or not quite as good as what I'd expect, or told me of delays in receiving responses).

Some of my colleagues and friends bought millions, others tens of millions, and some hundreds of millions (or Billions) during that period.Real estate is a funny game - it tends to go up, yes, but it does not always go up, and it can go nowhere for a decade or more, as a lot of apartment complex purchasers from 2021 are about to find out. 

I have gotten to know Matt very well over the years and consider him a good friend.

I don't know the Baltimore market but have a friend who is a very savvy investor there and maybe he would do some coaching to help you understand which way is up.