Hi, I have a recurring issue in Texas whenever I hire a plumber or handyman.

Screen well upfront...most residents who do this have a recurring history of it.

It would be unfortunate if the Wyoming LLC is the deed holder if the property is located in PA as I suspect you are likely getting hit with recurring registered agent fees (I don’t have direct experience working with LLC’s in Wyoming because there are absolutely no added protections incorporating in Wyoming but that’s my hunch).

On the psychological front, it sounds like you are feeling some anxiety which may be triggering "W2" thought patterns, which in turn may be triggering anxiety about falling into an "analyses paralyses".

How many people would you say typically attend these recurring meetings?

I can't imagine the stress/anxiety of positioning myself in such a way where I am reliant on a W2 income to buoy n > 1 properties, keeping them afloat month after month despite receiving a W2 income, hoping and praying life circumstances don't force a liquidation, especially in a rapidly changing market where appreciation is not a guarantee as supply continues to pile up and major metro STR markets continue to find equilibrium.

I was hoping to find a solution in our PMS or each OTA that would allow me to create a recurring rule, but haven't yet. 

I cannot make this Wednesday, but if it is a recurring event, I would love to get that information!

Hassle and anxiety factor is too great.  

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.