I would say take the shed, you'll find some use for it. I have contemplated this question also. I have a 20' x 11' basement shop, thats quickly loosing space. If you live in an area with a harsh winters (say the Midwest), does it make sense to heat the shop through the week if you are only working in the shop on the weekends? Or do you run the heaters just when you are working in the shop? What kind of heaters are recommended (radient, wood stove, etc.)?
Raphael Berrios is one of our Foundations of Woodworking scholarship students in Spring 2016. He also took our Timber Frame Tiny Home course and brought home one of the structures to finish for himself (you can follow his progress on his blog!  Here’s what he had to say about what led him to PTSW, his experience so far, and thoughts for the future:
Rocking horses, toy chests and dollhouses are just a few of the classic gifts generations have treasured. Now you can give all the pint-sized DIYers on your list those same classic gifts, and make them yourself with the help of these DIY toy kits. They're perfect for kids of all ages, and will be treasured for years to come. The best part? All these gifts can still make it to your door by Christmas.
to allow 9' at the peak, I like a "shed style" roof, but that may not fly in your HOA.I'd put double doors on or one large one, pour a slab, or use patio blocks then lay down Wolman. plywood for a floor, I would use foam insulating board everywhere I could, walls, floor and ceiling. A few bin type windows or sliders would let in light and fresh air. If you can't get away with your wiring idea, I would use a HD 30 amp twist lock extension cord with an "outside weatherproof outlet" mounted on the home professionally installed for code, 2- 8' long flouresent lights, and a 20 amp outlet inside for a heater and dehumidifier. Dehumidifiers draw about 5-6 amps. You might be better off with a small 6000 BTU window or wall mounted AC unit,( $100 on sale at the Depot), it will take the moisture out of the air and cool it as well in the summer. I'd use thin wall conduit around the shop with about 4 double duplex boxes. You may be able to bring 220v. in and then split into 2-120v circuits. If you make ANY dust in this confined space you must first catch it with a shop vac, then filter the air, and wear a mask. A bathroom ventilator fan would exchange the air and be quiet. A slab in front would allow sawing outside weather permitting. A roll up canopy over the door way would provide "shade" and rain protection. I know this sounds like a lot of work, but I know you can do it if you try. You can get plenty of "free" advice here and from an expert close to you. My neighbor enlisted the help of a handyman for building his 2 sheds and they became friends and did tool swaps and labor trades for time worked. My advice to you.. go 4 it! bill
The Community Woodshop allows me to have access to a countless number of the best quality tools in the industry. They are always on top of keeping everything working and running.  If anything breaks they are always very proactive in fixing things ASAP.  They also have more than enough tools so I never have to wait to use a sander or any of the smaller tools, and I have never had to wait more than a few minutes to get on the table saw (and even that is rare).
This trade and technical college currently serves over 15,500 credit students from its campus in downtown Los Angeles. Through the Construction, Design and Manufacturing Department, full-time students can enroll in a daytime certificate or an Associate of Science program in cabinet and millwork. Evening programs for current craftspeople include a certificate program in construction technologies and an Associate of Arts in cabinetmaking and millwork that provide students with the skills they need to work in construction or manufacturing.
I live in the second rainiest city in the country, Pensacola, so I am used to dealing with wet. I literally work out of my garage (read storage area, small woodwork area, washer/dryer...car? ). I wheel bigger tools and table out to the little covered area in front of the garage. I have an 8 x 10 aluminum shed that is strictly garden stuff storage. I mention this for two reasons.
With the top laying on the floor, bottom side up, the next step is to flip the base upside down, and attach it to the top. I followed Asa Christiana's design, in using s-clips. When I stopped by my local Woodcraft, though, they only had two packages of ten, so I didn't use as many as I would have, otherwise. For the top I put four on each side and two on each end. For the shelf I put three on each side and two on each end. If it turns out that I need more, I can always add more.

Students who are interested in woodworking, either as a career or a hobby, can find classes through certificate and vocational degree programs. Furniture making and opportunities for wood sculpture can also be found at schools that offer studio art programs. In California, a wide range of programs in the field are available, including individuals classes as well as formal educational programs. While degree programs include general education programs, all woodworking programs focus primarily on the development of hands-on skills with respect to safety measures.

Anyway, I'd like to know if I'll be able to keep (EDIT: and use) all my tools out there (current and planned) without having the shed become a rust-bucket for the tools and machinery inside. I'll have a 10" contractor's saw out there along with a drill press, a sanding belt, a router & router table, and lots and lots of old tools that I inherited from my Granddad years ago. I live in the Seattle area, so it rains A LOT. But I'm hoping that with the proper ventilation I can keep the tools in the shed dry.
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