Medford (North Boston) happens to be a low supply/high demand market so I absolutely need to get more comfortable with consistent rent increases but those increases need to be researched and in line with the market. 

I’ve noticed property owners who bought 7 years ago in these prime Denver spots often saw their values climb nicely, especially if they managed to keep consistent bookings.

Don't discount that.Real estate remains a valuable investment despite current challenges due to its tangible nature, long-term appreciation, and potential for consistent rental income.

Which then in turn consistently having 5 star reviews can increase your nightly rate.

@Reeti PeshawariaThis is a bit tricky to do since STR regulations are an emerging political topic so regulations are consistently shifting.

If you consistently analyze properties, recognizing a good deal will be much easier when it shows up.

You said you are new to real estate investing but you have a background in residential real estate - what does the background consist of?

If it's a company, how are they earning money and are they earning enough and consistently.

That's direction I'd advise exploring, not how to do it all yourself as an island, but as a facilitating power.

It often takes living and breathing the industry around the clock for a few years before you start seeing consistent returns.