To finally bring this thread full circle, I just received my Maryland certificate of Title today! It's been a long drawn out process. Between the time I spent learning about how all this was supposed to work, the time I spent working on the truck to get it fixed up to the point where I felt confident spending money on the titling process, and the time for the paperwork to clear, it has been 14 months.
I did go the International Title route. It took three attempts for them to actually get me the paperwork. The packet they sent me had a price of $590 handwritten on it by ITS after telling them everything about the vehicle and the $3000 bill of sale. I filled out the remaining forms and mailed them a notarized bill of sale (It's mandatory that it is notarized. $3 from a local packing/shipping/mailing company). Several weeks later, they called me to say that the price would actually be $890. I was stunned at the price difference. They blamed it on the GVWR. I mailed them the paperwork along with my credit card information (I used a credit card, figuring if I never received anything back from them, I had a means of recovering my money). They later told me that they were able to get it done for the original price of $590. After a number of calls over the next two months, I was finally told that I was waiting on the state of Vermont to get back to them. They also promised to mail the title and registration within 24 hours of receiving it from the Vermont DMV.
Several weeks later, I got historic Vermont plates, a 1-year sticker for the rear plate, and a Vermont registration with my Maryland address (why Vermont would register a vehicle to a Marylander, I don't know). All this and no title.... I called ITS again to ask about the title and to tell them that I needed it registered in Maryland, not Vermont. (They had told me they title Deuces in Maryland all the time and that it wasn't a problem). Their explanation to this was that I had to take the Vermont registration and the paper they included in the mailing explaining that Vermont will not issue a title for a vehicle 15 years old or older to the MVA. The MVA should be able to look up the law in their books, and see that they can infact register and issue a title for the truck. (I felt a little cheated at this point, I paid for a Maryland title...)
In hopes of making the process go a little smoother, I took everything ITS sent me to a local title company, Murray Title & Tag Service in Hampstead, MD. Murray's understood how everything worked and within 7 days was able to hand me the Maryland registration and historic plates. At this point I was told that a Maryland title was in the mail from the MVA and that I should receive it within two weeks. This cost me $140 in fees from the MVA and a $40 fee for the title company.
The $40 spent at the title company was the best $40 I ever spent on the truck, it was nice knowing I wouldn't have to fight the MVA and try to explain everything to the clerks there!
Today, about 1 week after receiving the registration, I got the title officially naming myself as the rightful owner!
I'm glad the ordeal is finally over! For anyone out there looking to title a vehicle, try to get one that's already titled, its a lot less stressful. For those in the same predicament I got myself into, the International Title route does in fact work for Maryland despite not having a title in-hand. It will take lots of phone calls, lots of patience, and some cash to make it happen.
Hopefully, this will help bring some peace of mind to those looking to go this route.
Thanks for all the help from everyone here who got me through the process!
-Kevin