Call a broker; costs nothing to ask, and you may be surprised.
One option might be to buy an aircraft, and lease it to a flying school who take care of insurance, maintenance, etc. + guarantee a certain no. of hours usage per month.
This way you get on their insurance, you know the aircraft is being regularly flown/checked/maintained and help reduce your overheads.
Seeing you are in the USA, I trust you are a member of AOPA? If not I would recommend it; they also have helplines to guide prospective first time purchasers.