Get proper training and I'm sure you could handle a 29 footer, but maybe not any 29 footer. It will depend on the rig and how she is set up, particularly if you intend to sail alone at times.
You want to have someone living aboard who works in the city, but how about yourself? Do you need to work? Sailboats are expensive to maintain.
I would advise being at a slip if you need to be on land every day. At least, I would want to be on a mooring with access to shoreside facilities, like showers and heads. I'm not sure what black water (sewage) discharge rules are by you, but near me, it would become a royal PITA to have to go to a pump out dock all the time. The nearest water where I can dump overboard in is 45 mins to an hour away in open ocean. You would want a marina or slip with a pump out boat that came to you.
If you are roughing it and will not have access to a marina, you really want to have a shower onboard. Many marine heads will double as a shower. You need freshwater tanks, a pump and something to heat water, which is not on all 29 footers. Speaking of this, you will need somewhere to go to get fresh water routinely as well, right? I think you would quickly find living outside a marina would require a ton of time wasting routines just to accommodate daily necessities.
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In the harsh marine environment, something is always in need of repair. Margaritas fix everything.