Looking to build a boots on the ground team that can really guide me in the right direction and be my eyes and ears.

I did a quick look and violent crime rate almost double that of Illinois as a whole. 

I guess it has to be fully paid back within 5 years from the distribution so you basically skip the first payment.)I vote that @Dave Meyer does a quick upgrade to the rental property calculator to include scenarios with simultaneous loans!

If they do not respond quickly when it is for rent, are they ever going to respond if there is a work order or some other problem?

As you mentioned, it might be difficult timing the sales of each of properties where you can achieve a combined exchange (multiple properties into 1 property / or a few properties).Just a quick note that may be helpful - I work with a group of investors that can help with a combined exchange into a single property and will buy it back once you've found a replacement propertie(s) as the final destination for your capital.

However if you buy in a neighborhood where people do care or all  your tenants have cars, you may get shut down quickly. 

I've only been to Texas a few times but it quickly became one of my favorite places in the US. 

Quote from @Brett Jurgens: @Jay HurstThanks for responding3.75%, 30yr fixedLike others have said, with that interest rate your best bet is probably to do a home equity line of credit (HELOC) to put towards an investment that you can quickly recoup your initial investment on.

Doing a quick scan off I see there are about 5k STRs in Colorado Springs (assuming you are there and not a neighboring town I am gonna say the town has minimal restrictions).

@Blake R.From my experience, land investing is a low-cost, flexible entry point but lacks the cash flow and quick appreciation of multifamily properties.