I went to your event in Orlando a couple years ago and it was eye opening for me.  

(Although if you're looking to use this money for real estate in the next 3 years, I would NOT put it in the market.)I'd be putting the additional money into a high yield savings account, and keep my eyes out for a great real estate deal. 

The protections which I would assume were made with acompassionate eye toward venerable renters backfired and brought outthe worst behavior from many tenants and have caused smallerlandlords to pull their properties from the market .

That is part of what I am paying the GC for, however it has allowed me to understand the process in depth, as well as keep an eye on costs.  

Rent: Focus on long-term rentals to generate steady cash flow, with an eye on market conditions for any short-term rental opportunities.4.

The issue is I've lived in cities my whole life and feed off social life, something I'm already concerned with having when I'm working remotely.I'm currently eyeing cities like Chicago and NYC, the latter of which I have not lived in and have been doing some digging on.

I also think it's great that our property isn't sitting empty when we're gone and because we own and live on-site, our neighbors also keep an eye out for us. 

If you're keeping an eye on the U.S. housing market, you've probably noticed some pretty interesting shifts happening lately.

My ability to picture and design something pleasing to the eye is lacking--a tool like this would be helpful, especially for ideation of what "could be."

Personally, I wouldn't totally disagree, but it is very much in the eyes of the beholder what "nice place to live" means.Based on your post, I would assume you are getting requests because you are a new landlord (maybe the old one was not a kind person, so tenants chose not to make any requests) and that you are asking them to pay more rent for a unit that is likely in worse condition than when they moved in.So now, you can either tell them no, or you can accommodate and potentially open up pandoras box of setting expectations that you will cater to all requests all the time, or as noted, you can remove yourself from the equation and hire a PM to handle the requests.