WTF should I buy (A consolidated list of bad decisions)

[Sijray21]

First TL;DR at the bottom

OK. Having some conflicting thoughts and I thought I'd solicit opinions. I've been tossing around the idea of selling the gti and replacing it with something fun and newer to mod and drive ('16 f31 msport, 16-17 golf r, 15-16 s3, etc.) that wouldn't happen for at least 10 months or so though. I'm the original owner of my mk6 2dr 6spd gti and I really like it and have been relatively happy with the car since I first brought it home (especially after the DG SS, intake, tails, and knob mods to personalize it). Having 4 doors and being auto would help out with lifestyle flexibility and awd would be nice to be able to swap cars with my wife for her take to work on snowy days since she's a nurse and hospitals don't close.

I've also been thinking of either getting a third vehicle and adding more mods to the gti for the fun of it. I wouldn't mind doing more work on the gti myself, but I'd feel a lot better about it if I had another vehicle working that I could use in its place. The wife's car doesn't work b/c she needs that due to the crazy nurse schedule. The future mods for the gti would be a tune, springs/struts, exhaust bits and a few other smaller things. The gti checks most of my boxes:

- awd
- auto/dsg (I'd still like to have a MT, but would like 2 cars in the household with auto)
-4 doors
- hatch / wagon / suv cargo (gti)
- hid/led headlamps, turn signals, and tails (preferably all LEDs everywhere) (gti)
- fun to drive (gti)
- tight-fitting seats (gti)

Cars I've considered for a nicer replacement:
15-16 f31 (msprt/lighting/dap)
16-17 golf r (dsg, DCC w/nav)
15-16 allroad (sport and tech)
15-16 q5 3.0t (sport seats)

Concerns:
- if I get a tune on the gti the clutch/flywheel would likely need to be replaced shortly thereafter (116k on the original clutch and they tend to shit a brick with a tune anyway).
- working on the car without a spare vehicle and doing something that leaves the car disabled since I really do need some transport every day (day care mostly since I can ride my bike to work if necessary)
- the gti has an oil-pressure-driven timing chain tensioner that is known to fail unless I update it, although I use oe oil/filter and change it every 5k and most of the techs think it'll be fine

I've entertained the thought of getting a third vehicle that my wife could also drive and something that would add some versatility to our household (auto and 4x4 - used truck or suv).

Options I've considered:
1. Don't do anything with the gti, get a newer nicer car next winter, sell the gti. I'd still lightly mod the newer car.
2. Buy an older, cheaper (<$10k), yet reliable, third vehicle for utility (extended full-sized truck, mid-sized compact truck, or suv) and keep the gti while modifying it further.
3. Get newer, low-mileage, third vehicle (daily that), sell the gti and getting something cheaper and fun, but still suitable to transport the kid (???) no idea.
4.???

Right now the wife has a golf sportwagen SE w/21k miles, so that should be good for a while. The gti has 116k miles and recently I've done all four rotors/pads, all fluids flushed, accessory belt change, and it's in great shape. The clutch /flywheel, pcv, and struts/shocks would be the next thing that may go.

TL;DR - keep the gti (116k miles and well maintained) and get a third cheap vehicle or sell later and get something nicer?