I suggest brainstorming your goals and clearly defining what attributes you are looking for in each property.

The issues I ran into was the local market was already flooded with STR's and in order to be profitable you had to stand out with a home that was either near an attraction (ie great view, Garden of the Gods, Downtown, or a College) or the unit had to have amenities (Hot tub, Instagram Wall, Pickle Ball Court) that would place your listing far and above other similar listings.I think you should strongly consider if you more interested in moving away and starting a life somewhere else, or in creating a cash flowing investment to supplement your income? 

Yes, I do agree that this niche is getting crowded now and we’d need to stand out to be looked at.

With the increased competition among sellers, it’s crucial to prepare a listing to stand out among the rest and work to address buyer objections prior to going on market.

You have to stand out from the competition to do well since there are so many rentals there.

In essence, this and dozens of other attributes are all baked into the cake long before I come close to acquiring it.

Each software I look into claims to have all three attributes (property, bookkeeping, project).

If there's thousands of STR, you must stand out to be successful!

There are so many experts on here it is tough to stand out, but picking say multifamily or 1031 specifically will help drive a ton of business.

Perform the same task in each app to ensure a fair comparison.Load a property with pictures and details.Market that property.See what your marketing looks like from the public's perspective.Submit a fake application to see how easy the process is.Run a credit/screening report on yourself.Enter a maintenance request, assign a vendor, and attach a fake invoice.Enter charges to the tenant's ledger.Enter recurring charges and automatic late fees.Sign documents electronically.Run owner reports.After testing a few apps, one should clearly stand out.