I could come up with a down payment for an investment property in a different state easier than my home state at prices are pretty high in the 300-400 k just for townhomes.

BiggerPockets also has a calculator to analyze deals, and I highly recommend you start this as soon as possible, even if you are not ready to buy.

This may come into play as you near the end of life and need to think about estate planning.4. 

Operated as an executive high-end rental for 2 years and cash flowed nicely while rented.

My endgame is to end up with $300k/yr in post-mortgage income in 20 years based on investments I make now followed by continued investments over the next 10-15 years own.

Some theming is basic and some is overdone, try to be unique or at least high quality, not a place you want to skimp.

Off street parking is typically more important for high end/expensive rentals.

Knowing the average bP buy and hold investor this type of information would be for advanced investors that deal in the back end of real estate not the front end like most who just want to buy a house for under market rehab refi rent or flip. 

BiggerPockets also has a calculator to analyze deals, and I highly recommend you start this as soon as possible, even if you are not ready to buy.

I see two high end homes for rent, 50k, 70k, 210k per month..