I dont think its too late for 2018 if you do this in late july- early September.
Never done anything like planning like this but whats involved? Find venue for what weekend event? How many cars do you count on attending, 500? I can tell you that if i come down, its going to be for either the full day or the night before or after the event. im not interested in driving 1,500 miles each way (MD) to spend a few days there. we all mostly have families so why does this have to be complicated.
Find Venue (big parking lot) let up come tents and get vendors and maybe a radio station to host and get a band out there maybe. what else besides a decided area that is close to lodging and shopping and food?
At this point in time suitable hotels are likely already booked for Labor Day weekend 2018 hence the suggestion to start planning for 2019 instead. You must remember most hotels do not have banquet facilities which are in demand for other events (think weddings, reunions, etc.) so there is a limited pool of suitable hotels to choose from. Obviously the Motel 6 or Super 8 will not work as a Fest hotel - have to go upscale to likes of Marriott, Hilton, etc. which have banquet facilities.
A suitable hotel
needs to include on-site banquet facilities as it is a custom to have a banquet as part of the TDI Fest experience. It is too much trouble to have everyone go from a hotel to a restaurant then go back to the hotel. Makes everything much easier/simpler if the hotel used provides the banquet hall and food.
There has never been 500 cars at a TDI Fest - if that were the case then it would be possible to hold a Fest every year as that implies strong support for same. I don't even know if there has been a Fest with 200 cars in attendance? You cannot compare the Fest with the Mopar Nationals, Bloomington Gold (Corvettes) or the many themed car shows at Carlisle, PA as the TDI fraternity while passionate are small in numbers compared to these other events. This is where your thinking may be flawed if you expect a TDI Fest to be the equal of these larger more professional car events which is not the case.
Some of us like to drive - I think nothing of covering 1,700+ miles (800 miles out, 800 miles back plus some local driving) in an extended weekend (Fri thru Mon) but I realize some people like yourself are not road warriors and wish to take a week to drive out, enjoy the event then take a week to drive back. That's nice if one has the time and money to do so but most of us can't afford to do that and still take other trips.
You're right, it's not complicated. The real issue is that
nobody wants to step up to actually organize/run the Fest which has been the recurring theme for the last few years. Basically everyone has suggestions to hold the Fest at such and such place but are unwilling/unable to help plan/organize same. That is the hard reality of the current climate for having another TDI Fest.
If you are truly serious about organizing a TDI Fest I suggest you contact member VeeDubTDI here as he can point you in the right direction to get started.