The safe play is cash out now when you know that you can. 

What should I be looking for (i.e. ability for tenants to pay online, online maintenance requests, how soon are rents paid to owners, etc...)?

If there are only small items, you may be safe to throw it away.

@Riley Burke I have an online VA Home Loans course for free.

Something like 65,000 apartments have come online since 2012 in DFW area and 24000 more under way and probably that many more in the planning stages.  

i.e. cafe, lounge area, art gallery space, co-working creative space.I would first like to:1) Build up a larger client base for my brand online and see the the need for a brick and mortar location2) Evaluate the trend of brick and mortar retail / coworking space going forward3) Store up enough cash reserve to accommodate the increase operating expense tied with a commercial retail lease4) Gain commercial residential experience which in my opinion has less risk of vacancy. 

We cannot accept the payment online (changing bank accounts) and they do not have checks. 5.

David said something that I'm sure I will never forget:Saving money feels safe, BUT saving money doesn't make you wealthy.

Most of them have their pdf brochures online you can pull up, zoom in..lol.., and read.

I realize I'm immediately taking another loan out and in the same position as before but I felt it was a more "safe" way to do it.