1) Is there a vacation destination you wish to visit most of the time or on a regular basis? if so where? No
2) Do you want to visit your home resort at least half the time, or do you want to trade more than half the time? Probably trade
3) What are your 5 top trade destinations? Grand Canyon, New Orleans, Colorado, Caribbean, Tennessee
4) How many people do you usually travel with - total, including yourself? 4
5) Can you travel any time, or are you locked into the school schedule? Any time
6) Can you make firm plans 12 or more mos. in advance? Yes
7) Can you vacation for a full week at a time? Yes
8) What level of accommodations do you prefer on a scale of 1 to 5 stars? 3+
9) How much can you afford to spend upfront, without financing? 2k-3k
10) How much can you afford to spend every year for a maintenance fee that will come due right after Christmas, and increase each year? 1500-2000
11) Are you a detail oriented planner? yes
12) Do you understand that once you buy a timeshare, it may be very difficult to sell or give away, and you are responsible for all fees, until you do? Yes
I think you might struggle for "Grand Canyon" - I don't know that there are TS near there. Otherwise, I think Wyndham - Club Wyndham Select at a lower MF/Pt resort could work well for you. They have New Orleans, Colorado, Caribbean and Tennessee. If you're ok sharing a 1BR such that the other 2 people sleep on a sleeper sofa, I think you can certainly hit your budget. If you need a 2BR you might have to stretch for New Orleans to try and get the points needed under $2k a year. There are semi often various Wyndham give-aways on TUG in the free TS forum, but check the MF/pt offered. For La Belle Maison in NOLA you're looking at ~329,000pts for a 2BR for a week. Usually the points on offer tend to be around 300,000ish or 405,000ish that's near that value. Good news, you can for a small fee save points into the next year, so you could reasonably go to like Tennessee for ~ 148,000 pts and then use the saved points to go to NOLA the next year, rinse and repeat. Look at their website and you can download PDFs of the point charts for each resort. 1BR options are going to put you under 200K in many locations in some seasons. You should be able to get 203,000pts for around $2k a year in MF if you hunt a bit. Buying them might cost a bit for really low MF/pt ratios, but you can also sometimes find some in a giveaway for pretty good rates.
The other option I think is worth considering is RCI Points - if you're OK with 3* you can look for a Grandview or maybe high points value Massanutten contract that's already in RCI points. Make sure to get them to transfer. These can be had sometimes for just covering the transfer fees of around $700. MF can be around $1,000 at Grandview for 98,000 or more points, I believe the Massanutten one I saw was $1,600 for ~160,000 pts. IDK how expensive the Massanutten is to get - again, look for what's on offer on ebay and at TUG.
RCI points is a little more confusing than just using Wyndham points. You have a bit more random availability, but locations all over, including you'll often see like Wyndham Smoky Mountains available. If you go "last minute" you can see RCI points costs under 20,000, some under 10,000. However, you have to pay for an RCI account ($100 a year) and pay for each "booking" - right now it's $299. And when you get to the resort you often have to pay resort fees of about $110. (varies with the resort). That said, while there's a lot of "nickle and diming" the actual cost can be quite low. Let's say you compare Club Wyndham Smoky Mountains 2BR. While there's less availability than direct with Wyndham, Wyndham wants 148,000 Wyndham points to book. At a "easy to get MF/Pt ratio" that would work out to around $1,100. At a reasonably easy RCI Points like Grandview 98000 2BR, you are looking at 53,000 RCI pts. That's about $596, plus $110 resort fees, and $299 exchange fee and tax. That would work out to $1,030. It sounds like a lot of extra fees, but in reality you're paying around $70 less than direct, at the cost of less availability. But you get the benefit of no only having Wyndham locations, and getting better rates at all other RCI locations that via Wyndham corporate.
I think Wyndham is a bit better in availability an ease of use, and it still gets you RCI access (just at worse point value rates). You can always look for Last Calls and Extra Vacations for cash too.
