We're a 2 man shop providing 2ndary education to a very targeted demographic. I'm the only programmer / sysadmin / anything technical.
I originally developed the website with a separate mobile version using some code to detect the type of device and decide to redirect and when. This, is a pain in the butt as i'd always forget to make changes to the mobile version when i changed the main site (A LOT on my plate)
I'm in the middle of developing version 2 of the site and developing the main site side by side with mobile devices so 1 site can do both desktop and mobile.
When this new version is done, I'll finish developing the iOS native app (i've started it, but put it on hold for the new ver 2 site)
1: I want both a mobile version and a native version - I feel a native iOS app will provide a better experience - BUT - i also think i'll run into the same problem as before; updating the main site and not updating the ios app - maybe by that time i can hire another programmer... As i'm a Apple user, I have multiple iPhones / iPads / iPods to test on. I don't even want to think of how many devices I'll need to build a proper native Android app.
2: I'm never happy; I'm constantly re-writing my code, persuing new / better ways to do stuff; i'm never done. Technology choices are always my choice but I make sure my partner knows why i'm doing something and hes open to question anything he wants, especially if it requires money / time / blood.
3: Version 1 was full steam a head, lets get it done and out there. It has a lot of short-comings - most of only i as a developer know of but some visible. Version 2 is much more planned; I took the time to build prototypes, play with different ideas, think about why i was doing something and not just programming away. I'm happy i'm moving to a scalable main website and i'm pretty happy we'll have our first of 3 planned iOS apps (native app, game and magazine). I try not to do things I'll regret, but making a mistake in the process of learning is ok.
4: How long building such a site would take as the only developer with a day job. I'm committed and hopefully the payout comes someday, but being the only programmer on a fairly large project kinda sucks.
5: I collect as much analytic information as I can. My data to date shows me the vast majority of my users are iOS users (reason for native iOS app), are between 20-30 years old, etc.. Someday it'll be monetized and version 2 will have interactive interfaces.
I'm not done yet so you can't see it!