The high end rental properties can be a different animal than your run of the mill $2,500 month rental both in terms of upkeep and demand.

I know a lot of Chicago investors are here too; but if you were in my spot would you recommend Chicago as prices are too high and I have never been to the city moving next year.

My known options are hard money or private lending and then maybe doing a cash out refi, but rates would be high on both ends and will really cut into my cash flow. 

There's a lot more competition than previous years, and prices are high.

I assume it’s not high enough that you or any family members want to take on the job?

Some high-end STR's (like in Joshua Tree) do use professional models, but for your market and property type, I’d suggest removing personal photos and focusing on the space itself, so guests can imagine themselves there, which is really what you want.You also have 81 photos, that’s too many.

@Emily Gowen so as you pointed out you would not have to do a 1031 exchange on your current home to avoid the capital gains tax and coupled with what Dave Foster pointed out I think, speaking from experience you would have a high likelihood of success. 

Just be aware it's highly unlikely the hourly rate will be negotiable.

With big benefit potential of possibly retaining "Graduated" persons who are now highly trained, proficient employees. 

Crime in Little Rock is significantly lower than most cities it's the way the city is zoned it looks high based on the old city limits and population.