Welcome to the club, Timothy, or is it Tim?
Looks like you live just north of 36 and west of I-25 on the north-west side of Denver.

David Rowland lives up your way, and flies a 150hp 150.
I used to have a 152 and I loved it. It wasn't much of a real load hauler, but it got me in the air, and was a lot of fun. I fly out of Arlington, TX, field elevation 630 feet.
I bought a 150/150 taildragger in 2005, and I have to tell you....it's the best thing since sliced bread. There are, however, other pilots on this forum, better pilots than myself who will have absolutely nothing to do with any taildragger, much less a converted 150 or 152.
You can find nice 150/150's out there, both in the nosewheel and tailwheel conversion configurations. My thoughts on your location...realistically...every time you take-off, you'll be relying on the engine horsepower. You will be much better served finding a nice 150 hp plane. Every time you take off, you'll be glad you did. Every time you take-off with a passenger, you'll be doubly glad you did. And, when you take off with full fuel, two people, and 120 pounds of baggage, you'll be amazed. That, I can promise you.
You can find decent 150hp planes in the low 20's...I found mine (high time airframe and high time engine and tailwheel) for 17K. Look around. Things to take into consideration while looking for the 150/150's, since it's a conversion, is paperwork. You have to be very particular that you get at a MINIMUM
ALL FAA Form 337s. They are the official records with the FAA that show the proper approval of your particular modifications. If you find a prospective purchase, order the FAA CD ROM of all the official FAA documentation. Then, when you and your mechanic sit down and peruse the books, compare what is in your hand with what the FAA says should be there.
Buying an airplane is tough sometimes. You don't have the resources to scour the country, visit EVERY potential purchase, and pick the very best deal. And, you'll likely fine a nicer, cheaper one after you buy one for yourself. So, it's like a marriage. Find several to pick from, buy the one you like, and then close your eyes.

Why the huge difference in price? Engines should be overhauled between 1800 and 2000 hours, unless you go strictly on condition. Then, it could be anywhere from 50 hours to 5000 hours. Avionics is a concern. You'll at least need one com, a transponder and an encoder. Or, you can find a 150 that has an avionics suite that rivals the space shuttle. Paint and interior are other significant variables. You can figure on 7-9 thousand for a paint job, and between a thousand and fifteen hundred for an interior.
Bottom line...just as you've seen with the conversion prices, find one as close to what you want, and go for it. If you wanted to buy something and make it what you want with an engine overhaul, new snazzy paint job, new avionics, new interior, and full LED lighting, you'll quickly discover that you've invested money that you'll never recover.
Back to the subject of flying taildraggin' 150's. As others here can attest, the quality of the conversions, since they were all done in the field, may vary. Gear geometry seems to be the absolute key ingredient required to have a well-behaved taildragger. The good thing is that it's relatively easy to work out. Time consuming, perhaps. But the real danger is pilots not keeping up with the increased workload of tailwheel proficiency. It is quite the perishable skill.
I pay almost 1000 dollars/year for insurance for my 150/150 tailwheel. I've got quite a few hours in the tailwheel, too. I only paid 525 dollars/year for my stock 152. So, insurance will be a factor...easily adding 10 dollars per hour to the operating costs.
Another recommendation...give David Rowland a call. You're already flying a 150hp 150, so you well know the performance edge of the larger engine. Go visit him, talk to him about his experience with the 100 hp 150 vs the 150 hp 150. Get the minimum avionics needed for the job, and invest in a good hand-held GPS with XM weather capability. You'll have the tools you need to make your plane a real asset.