I can have them just setup an ACH for the monthly payments, etc...but I feel like this would be easier with some automation, and there just must be something that's already setup for this.

Vrbo has free price automation software.I use Excel for book keeping.I don't pay for any third party software, not really needed on 1 or 2 properties.I charge a little extra for cleaning fee than actual cleaning costs.

But I have many automations set up and have very detailed financial statements I generate every month so it definitely took me a few months to get the hang of it.

It's automated, secure, and reliable.

It is a fairly automated process for them

There are other options such as harvesting capital losses on other financial instruments, but the stock market has been pretty good lately, so that may not be an option.

Given your high income and time constraints, consider exploring businesses with semi-passive models, like investing in syndications or owning automated online companies.

Sherman, and Denison are growing a lot due to the Texas Instrument chip plant being built there.

All you get is what you can export/import via CSV file:(We use Propertyware, have experience with Buildium, and have played with Appfolio and RentManager.Buildium is for smaller companies.The other three are tied, the differences being how much automation & customization you want to do.If you don't see yourself growing beyond 150 units, go with Buildium.If you're not very techy and plan to grow over 150 units, we'd recommend Appfolio.If you're techy and plan to grow over 150 units, we'd recommend Propertyware or RentManager.Of course, schedule some demos, take GREAT notes and them make your decision.FYI - there are MANY new options on the market, RentRedi, TenantCloud, Apartments.com, Hemlane, Rentec.

I have great properties that sell themselves.I love the analytical tools and free price automation Vrbo provides.