In areas with a lot of market activity, there will be more comps to choose from but please remember that CMAs also include active listing, under contract and expired data (not just sold data).Connecting with an agent who specializes in your area(s) of interest could be helpful here.We use 3 platforms, including our local MLS, to run CMAs.

I help engage brokers to find new locations, complete due diligence on prospective locations, and collaborate with landlords to ensure we are on-time with our contractual obligations. 

You say this would be when your flip sells...flips are inventory in an active business, not investment, so they cannot be 1031'd.

Appreciation with the Fed actively trying to push rates downward?

My SEO skills are definitely not the best and while I use Instagram, too, I've found it hard to get people to actually engage.

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The key factor is ensuring the property qualifies for favorable tax treatment by adhering to IRS rules regarding short-term rentals and material participation.For the 7-day rule, the IRS requires that:The average guest stay must be seven days or less for the property to qualify as a short-term rental.If the average stay is 30 days or less, you must provide substantial services similar to what hotels offer, such as daily cleaning or concierge services.Regarding material participation, to further classify the income as non-passive, you must meet one of the following criteria:You spend more than 500 hours actively managing the rental in a year.You manage the business yourself and spend at least 100 hours, with your involvement exceeding that of any other person involved in the rental.Please note there are actually 7 ways to qualify, the above two are the most common.

They are a young engaged couple, and we actually have a few acquaintances in common (a connection we discovered when they were moving in). 

Particularly on larger balance CRE (Commercial Real Estate) this rate improvements can lead to a dramatic increase in activity and investability. 

Yes, you'll have some costs and time spent to keep your license active, but having your own broker's license would give you extra flexibility in the future.