Looking to expand my network in San Antonio.

If they are professional, they can explain this quickly and easily.

@Greg Friedman if you weren't moving abroad and were going to be within an hour of the property - you could easily DIY manage it.Otherwise, you will need either family & friends or a PMC to handle:1) Emergency maintenance issues2) Tenant nonpayment issues (eviction)3) Showings & maintenance when the property is vacant4) Preventive maintenance issues5) RentReady repairs between tenants

I wouldn't necessarily call myself new to real estate, however I am wanting to expand and shift directions a bit. 

Start to expand your network#2.

Make a list and look closely at each one to see if they are an option.If you can't find someone within your network, expand your network.

I am in the similar boat and planning to expand to other areas to scale up. 

Would you build a portfolio with long term rentals prior to investing in short term rentals, or would you use short term rental opportunities for quicker profit gain to expand on purchases of long term rentals.

How can I better automate my lease agreement being sent out, information filled in, and then easily signed by the guest?

You can easily do this on a spreadsheet, and it will take less time to track than finding and learning new software.