Anyone work in the wine business?

[hownowbrowncow]

So I have 9-10 years to go until FIRE (4% withdrawal number) assuming nothing changes in my current calculation variables.  Like others, many days I find myself daydreaming post FIRE life.  I would be in my early/mid 40s.  My thinking is that once I hit FIRE is to transition out of my current line of work and into part-time work.  "Working for fun" is a loaded phrase but I guess that's essentially what I'd want.  I'm not going to turn down my paychecks but the point is I wouldn't need them to my cover living expenses.
   
I am an aspiring oenophile and could see myself as an hourly employee in a tasting room - undecided about retail offsite tasting room or one on a vineyard.  Punch in, punch out.  Work hard on the clock but leave work at the office.  I'm not naïve.  I know one person's fantasy job is another person's nightmare so I want to think this through and would like to hear from people who are in that world.  I can't really ask people I know in "real life" because explaining the whole retiring early thing just sidetracks it and I wouldn't want to insult anyone by saying I'd do their job for "fun" and not the money.
   
Side note - All my post-college jobs have had relationship management components (i.e. customer facing - just those customers aren't retail consumers).  Also I did work retail (sometimes full-time) for a nationwide clothing store (rhymes with "App") from age 16-22 so I'm not a newbie in that sense.  Won't be super relevant two decades after the fact but the point is I get being on your feet all day, working a cash register, dealing with annoying customers, etc.
   
So questions for anyone out there  who knows the answers-
   
1) If you were the hiring manager what you would think of a 40-something with no previous industry experience (MBA, 20 years of project management/finance work) who applied for a part-time job in your tasting room?  What kinds of things would make you take her seriously? Adult education courses?  Experience with events from her volunteer work?  (I'm on a few boards)
*This is the main one*  I have about ten years before this point.  What kinds of the things should I be doing so I'm not starting from scratch ten years from now?
      
2) Would it be a deal breaker if she wanted to keep her hours 20-25/week with minimal nights and weekends?  I'd like to be a daytime employee.  I'd absolutely pitch during peak weeks but I wouldn't want a situation where I'm expected to staff every wedding held there (if at a winery). 
      
3) Would seasonal work be a good fit for me?  I feel like that's the type of set-up where you are expected to work the most nights and weekends.  I'd rather have half-time hours year round and maybe take off a few weeks here and there when the business is slowest and it would make sense to reduce payroll anyway.   
      
4) Would the MBA/previous experience be an asset at all?  I'd also be willing to help with the books/back of the house stuff on an occasional basis.  Again I'd want my main work to be "front of the house" but I do love Excel. 
      
5) Would it a deal breaker if she can't lift more than 25-30 lbs.?  That's about what I can lift now.  I'm healthy just skinny and lacking upper body strength.  I'm hoping I don't deteriorate too much in ten years.
      
6) Undecided on location.  Default is to stay in Seattle/Woodinville area but open to other areas.  Of course California - my previous home state - comes to mind.  I love the central CA region (Paso Robles through Santa Barbara) but state income tax/cost of living increase would be a pretty material change.  Big Sonoma/Mendocino fan but again $$$.  I know places like North Carolina/Virginia are new hot wine destinations but I would never fit in in the South - hell Washington state east of the Cascades might be too red for me.  Obviously any major city in the US now has wine shops/tasting rooms so being in a wine growing region/adjacent area isn't required but I do like that climate and geography. Recommendations appreciated.
   
Do I sound too entitled or demanding?  Any attitude adjustments/reality checks?  Like I mentioned, I haven't worked retail since I was 22 so I've been out of the game for a while. 

[protostache]

My mom did this for awhile after leaving her teaching job. She had zero wine experience, just a lot of past retail jobs and a personable attitude and did fine.

About location, woodinville in particular has a bunch of wineries and tasting rooms doesn't it? I'm sure you could find something that matches what you want just by asking around. They all probably have a ton of part time retail help.

[Apples]

I'm not sure if you'll just be able to waltz in and not expect to work weekends.  Most places have a seniority system where the employees that have been around longer get to choose their shifts, and unless they really need tip money they probably will choose the weekday shifts.  The fact that you can do books will depend on what they need, but it would be helpful to advertise "hey I can add the cash registers and do billing and enter inventory in excel if you need me to".  That might get you into weekday shifts.  I would expect seasonal labor, but I live in the Northeast so I'm not sure about west coast winter weather.  Being 40 with no previous experience might not be bad if you're knowledgeable about wines.  My husband works in the beer industry and has a certification in brewing, but also knows there is a lot to learn on the job.  I think that got him hired over some people who were bragging about their certifications.  The brewery was interested in someone able to serve beer to customers and chat them up while teaching them about craft beer.  They turned down guys for serving and brewing who were full of themselves and had demands for the job.

After all of that, I think you'll find what you're looking for if there are many wineries in the area and possibly if you lower your expectations about working Saturdays.