Hi Soyoung, Consider consulting with a real estate attorney or property management company familiar with the area.

Note local you can self manage.  

What do you use to manage the calendars to ensure that if the jumbo listing is rented both individual listings are blocked?

Also, are there any recommendations for investor friendly Real Estate Agents, Lenders, and Property Managers in the San Antonio areas?

Do you use cozy or another PM platform to onboard tenants and manage property?

Plus I network a lot with people and hear how things work for them.Anything deal with managing, either flips/rehabs or properties would be great too.Maybe an AP/AR Position for an investor, an entry level management position, PM assistant.

It is also very inconvenient for you to manage one guest putting utilities in their name then within a short time frame having to make sure all of those utilities get switched over to the new guest.

There’s also plenty of property managers to help you remotely manage the property if you do end up moving.

We are self managing and cleaning ourselves.  

Allstate (captive) is not a good place to be if you need any sort of sophistication with your risk management