If it wasn't for the dogs, this sounds very doable, and this is how:
- you need to have the flexibility of moving a trip one or two forward or back. Weather in the midwest rarely remains unflyable for more than a day or two, this is not like the coasts where you can be socked in for a week.
- you need to have the willingness to leave your plane at the outstation and rent a car if the weather doesn't support flying and you need to be at your other shop the next day. Come back when the weather passes and pick up the plane (costs $30/day).
- you'll probably need icing protection. In your budget, that means a booted 210, a booted A36 or an A36 with TKS (well, the last one is outside of your budget). If you can stomach higher direct operating cost, a Seneca could also do the job. If you fly 300+hrs/year, you will have no difficulty remaining current in a twin, it'll just cost more to operate on a per-mile basis.
In the end, you'll be best off
- finding a dog-sitter
- upping your purchase budget by 100k
- buying a SR22 with inadvertent TKS and DFC90 autopilot
Talk to an aviation tax professional. While you can't take bonus depreciation on a used plane or expense the purchase (like you could on a new plane some years back), buying a used plane and flying it for business will still have quite a tax effect. Like any other vehicle, you can still depreciate the value of a used plane on a MACRS schedule and all your flying and recurrent training expenses are direct business expenses. So while 'upping your budget by 100k' sounds like a flip recommendation, if you have a professional look at it relative to your after-tax expenses over a period of 5 years, the difference may be a lot less.