[TriLUG] chromebooks for small biz

[Dewey Hylton via TriLUG]

over the past year or more i've read more than one person on this mailing list
extolling the virtues of chromebooks for grannies and kids alike. my target is
a different audience - small businesses. 

i have several small biz customers which are very different from each other from
a business standpoint, but very similar in an infrastructure kind of way. most
are more or less married to a single (and badly written, i may add) windows
application which basically runs their entire operation. despite being in
completely unrelated market segments, the software these folks run all have the
same issue: runs only on windows, and REQUIRES ADMIN PRIVELEGES TO RUN. *sigh*

so for each of these cases, i have the app running on a terminal server which
is locked down to the point where the users can only run the one app, and print.
some customers run normal desktops, but most of them actually run raspberry pi
thin clients which are basically just thin clients - login at the text console
and end up with a windows login screen for the terminal server. samba is used
for home directories and nt4-style domains providing their network credentials.
very simple stuff. their mail services are provided by zimbra on a linux server.

two customers are now wanting access to their one application from either home
or for their road warrior salespeople. i currently leverage openbsd's ipsec
for office-side vpn, and the company owners connect to that with their mac or
whatever desktops. but they want to provide laptops for specific users to be
able to access this one app ... so i'm looking at a combination of chromebook
hardware and possibly either a straight rdp session over vpn or something like
guacamole for web-based sessions. ideally they'd be able to use their normal
corporate credentials to authenticate to the chromebooks but i don't see a way
for that to work.

so ... 

1) has anyone seen a way to connect chromebooks to their non-google directory?
2) can anyone recommend a chromebook-friendly ipsec vpn client not tied to cisco?
3) favorite rdp client? one which has baked-in support for vpn or even ssh would
   be great ...
4) recommendation for something other than chromebook (light/cheap linux?) which
   could get the job done while not tying everything to google?
5) recommendation for chromebook or linux laptop which has its own internet
   connectivity built-in (not requiring another hotspot)? i bought one many years
   ago and still have it - great in the past but insufficient for this task:
   https://esupport.sony.com/US/p/model-home.pl?mdl=VGNT350P
6) flames >/dev/null (samba3/nt4? yeah, i know ...)
7) something i forgot? i'm sure there is plenty in this category.

thanks for your consideration.