Welcome Jeffrey Ginsberg Your current profession, past/current experiences, and the network of folks that you interface with should be some great resources for your investing.

Apparently it has a seamless interface with google maps/street view.

It's not as professionally done or have the same interface but are you getting 5K more on a purchase price to go that route.  

The user interface is less important than the content and search engine optimization of your site.So choose whatever system you feel comfortable with that gives you a reasonable amount of control over the content and meta data, and focus your efforts on SEO so that you actually get some traffic to the site from which to capture leads.

It can be helpful to work with a company where you interface with a list broker.

Also optionally allocate across only subset of properties, e.g. mowing lawn for a duplex, that charge only gets allocated to those 2 doors.2) Download from bank and credit cards, and then what's the interface for quick bulk tagging - we currently tag each transaction by expensetype and property so thats 2 attributes per transaction, so how long would it take to tag say 100 downloaded rows all at once.3) Generate monthly journal showing rent payment status by property so we know who hasn't paid and needs followup text and/or a 3 day notice.4) Separate out management reports from tax reports.  

I only own in Oakland but I check out this site to see how their analyses and buyer interface have been evolving. 

That said - you mentioned "chores" - the board should just be overseeing the management company, the funds, interfacing with the members.

Here are some of the ones I use frequently which have a great user interface without unwanted ads, etc. and are all free:Mortgage Calculator Plus - allows you to quickly look up mortgage costs (principal and interest) and from there, has a very handy feature on add in extra payments, taxes, insurance, etc. ..

The online interface is a little clunky, but it works.