I would spend money to enhance and update to current standards the search functionality and person to person tagging so it's easier to find stuff.

If I had tried to scale my business before I understood what was required in hiring marketing expertise I would have made the same mistake as my friend of hiring a “generic” on line marketer and probably ended in failure. 

I found it researching online after many months.

Its not my money. 

I have integrated a couple of other platforms and had to do the exact same steps when it came to being able to receive payments online.

If you decide to revisit STRs, you might want to explore properties where you can project expenses independently, such as using local STR forums or online tools to estimate maintenance, management, and occupancy costs.For networking and strategy-building, you might find local meetups or groups beneficial.

There are also many online calculators you can use if you do a search for them.

But this was late 90s so way before on line stuff had taken off.

Anti-money-laundering laws are largely to blame.  

Once completed, the goal is to get them rented and then pull money out of each house to build a high performance spec.