I grew up burning wood and have continued, as I enjoy it, the heat, and the work. When I built my house, I installed radiant heat everywhere, i.e. tubing in the concrete. For the first 7 years in the house, I burned wood in a Lopi Liberty woodstove, and typically the house was always cozy, sometimes too cozy in the shoulder seasons, but never cold. Always at least 72. I'd burn enough oil in the boiler to keep the concrete at a minimum temperature of usually 66. Typically it was always warmer than this from the stove alone...though on the coldest of nights the oil would surely come on. I think I burned maybe 100-150 gallons for the floor minimum temp. The house is very open, so heating with the woodstove is very easy.
A couple of years ago I built an addition and an attached garage/shop. The addition would be poorly heated by the stove, as it is a few feet lower than the mainlevel of the house, and also it is separated from the house, with a 5' open doorway between the two. But clearly it would be darn chilly in there if trying to use just the house woodstove. Plus, the garage/shop is pretty big, 2200 sq ft, and I would like to be able to heat it someday as well for winter working (mainly to finish the house and whatever happens when that hobby is done). The prospect of heating the addition with oil is bleak, and I'd never burn oil to heat the shop/garage...I'd rather freeze while working. The addition and shop/garage all have pex in the concrete. It is possible to heat the addition with another woodstove, but that would involve two fires, twice the inside mess, etc. Not something my wife was fond of.
So I took the plunge and bought the outdoor gasser, namely a Garn. So now (or at least when everything is insulated and ready), I can heat the addition, the house, the shop/garage all from the Garn. I no longer have to have the mess of the woodstove in the house. Even when you are careful, there's always a bit of a mess.
I thought I'd miss the woodstove tremendously, as I grew fond of standing next to a blazing stove for the instant warm up. But honestly, having not had a fire inside all of last year, I don't miss it. And I certainly don't miss the mess...and no worry about a chimney fire, though I never worried about that really with seasoned wood.
So, you asked if folks with a woodstove went to a boiler, or vice versa. I did....and I'm very happy I did. Obviously we burn more wood to heat everything, and there is the inevitable loss with underground piping and whatnot, but that can be minimized. It is a big financial plunge...a good outdoor gasser is typically at least $7K or so, and that is just the beginning. Storage, piping, controls, insulation, etc. It all adds up pretty fast. I'd count on at least spending 50% of the boiler again, and like a full 100% again, but it depends on your system. So you have to ask how much it is worth to you. My Dad asked me just the other day what I based my calculations on as far as financial return. $4/gallon for oil. If I heated the addition, that's easily 500 gallons, plus the other 100 for the house floor minimum, plus DHW....so it all adds up to say 1000 gallons a year, or $4K. And I haven't heated the garage/shop at all....and who believes oil will be $4 for the next few years? Plus I can't receive oil once the snow flies, long driveway, so I'd have to have another tank installed....and where? Etc.
So to me it is worth it, but I can cut my own wood for "free", and I enjoy the work...most importantly. It is a pleasant hobby. If I didn't, it would make no sense....unless wood was very cheap.
I do agree with the others, seasoned wood is likely going to improve things for you. A gasser would have you burning less wood, perhaps by 30-50%? The estimates vary.