Our home is in a way nicer neighborhood and schools but it's a large 1961 builder modern that we purchased from the original owners estate.  

The property I'm interested in has been fully gutted and rehabbed, so it has the charm plus all the modern amenities.

CDD’s are mostly used by developers today to build large, highly-amenitized master planned communities to satisfy modern lifestyles.Let’s see how CDD’s typically work today.

They look quite modern and even in this older home (high ceilings) heat the rooms very well. 

I could be wrong.If I'm starting out I would pass on this and find something newer, more modern.

Cbiz and proper are the big onesAmerican Modern does itForemost does itNationwide, safeco and other similars MAY do it as a rider but also may limit you.

My initial thought is being able to "inspect" damage or a repair by having someone video it and send you the video, or you could watch live and ask questions.Second thought is having typical security cameras in common areas and being able to remotely review footage when someone has a complaint, at least to get a sense of what's going on.Seems like with modern technologies there should be some clever approaches that make remote management easier...Speaking of which, @Ryan Swan, there are electronic locks you can put on a door such that you can give a person a one-time code, and you get a record of exactly when they entered and left.

Re: Only pulling down to 20 degrees below outside temp.I don't know what kind system you have, but...In my personal residence I run the A/C at 69 when it's over 100 degrees outside 24/7 with no problem at all.It pulls down the temp to wherever I want it.I have a lot of insulation and modern double pane windows.In the winter I run the forced air part of the system at 72 when it is 20 degrees outside with no problem.Good Luck!

The answer to your question is YES, recessed lighting looks more modern, BUT it's not necessary. 

At $475/month I would also think the units are very dated and substantial modernization and improvement ($$$) may be necessary to bump the rent up.