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Contrail is solid shelter, my buddy has one

Yeah. Had a Contrail, have a ProTrail. I'd love to have something that good in a side-opener. Wasn't a thing when I was younger but now that I'm older and stiffer, getting in and out of the big end of a tapered tent, then getting turned around to get feet to the small end is more of a pain in the ass than I'd have imagined. After a real long, hard day of hiking that little maneuver can be the final straw for throwing a hamstring cramp. F-u-c-k .. I hate cramps.

^ all my shelters are now side opening, even my winter tent

What is your opinion on using the Tarptent Aeon Li for late Oct, early Nov elk hunts?

I've had mine out in some pretty rough weather, but I don't think I'd choose it if snow is in the forecast. I've had it out in light snow and it's done fine. I've had it in some pretty windy conditions as well, but there are definitely more bomber tents out there for "bad" weather.

I purchased a used Tarptent Stratospire Li last year and that's the shelter I'd probably grab for late October (in Montana anyways). Has more room, double walled, double vestibules and stands up to rougher weather better. Still pretty svelte at under 2 lbs.

Kifaru Paratarp works well.

https://www.precisionoptics.net/Kifaru_Para_Tarp_Coyote_Brown_PHTP101_p/phtp101.htm

https://www.rokslide.com/forums/threads/wts-kifaru-paratarp.46008/

I remember a thread about the Paratarp, Kifaru had a vestibule for it, you used sewing pins the pins with heads on them to hold stuff in place.

A guy used the set-up in some sporty winds, had quite a few nice little holes from the pins every few inches. He wasn't happy with the vestibule pinned on deal.