I have read on occasion that it is good to re-set the windows in your older Hi-Lo. Since mine is an 1986, should I plan to do so? If the answer is yes, then how do you go about it?

Not sure how your windows are fastened in, but on newer trailers, you unscrew the trim piece inside the trailer and then remove the window. Use Butyl rubber tape around the frame. You will have to remove the old sealer.

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Rich
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(215TL) - 1995 21' TowLite
(2209T) - 2009 22' TowLite
(2510 ) - 2010 25'

May want to do it as a two-person job, a person on each side of the window so it doesn't have a chance to take a fall.

__________________
Les & Patricia
2006 22ft towlite (replaces 97 21TL)
2006 Toyota tacoma pre-runner 4.0 L V-6 quad cab
w/ 98 chevy Powervision towing mirrors
2017 Chevy Silverado 1500 5.3 v8 (replaces Toyota)
2 Hobie mirage pedal drive kayaks

I have a 1990 25ft. Classic HiLo. My husband and I have removed five windows and will do the remaining three in the spring. You are absolutely correct that this needs to be done on older trailers. This is something that is a do it your self job. It takes two people to do it. Start on the inside by removing the screws from the trim ring.Have the person on the outside steady the window. Loosen the trim ring with a putty knife. Go outside and gently use your putty knife under the edge of the window working all the way around until the caulk and the window lets loose for removal. This can be done in a lowered position. Have a table ready or saw horses with a sturdy sheet of lumber on top to place the window on. Two people ease the window out and place on the table. Need a step ladder. One person can be cleaning the side of the trailer off,remove old caulk butyl tape. The other person can be using a stiff putty knife to remove as much butyl tape as possible. Doesn't have to be perfect. With the window out you will see the construction of your trailer. See if the walls have any water dammage or delamination. Purchase a tube of Lexell caulk. Purchase butyl tape ahead of time. You may want to wrap the edge of the window two passes of tape. Put the window back in from the outside. It is perfectly normal for some butyl tape to squeeze out. Remove excess with putty knife Caulk on outside with Lexell caulk. Go inside and put trim ring back on. You may want to invest in stainless steel screws to reinstall the window with. After traveling it would be a good idea to check all your window screws to see if they need a sl. tightening. You may want to leave the window for several days to let all the butyl tape squish out. Scrape off excess and then caulk. If your trailer has an emergency escape window as part of the window this can be resealed with weather stripping and then do the window as I have described. Our Air condition box on the outside was a big source of water leak/delamination. Really take the electrical cover off/drill out rivits.We were able to get a new part from our RV dealer. I would also advise you to scrape every inch of exterior caulk off and clean the area and reapply lexell caulk. It is a bit scary the first you take a window out,but yopu can do it.
Youtube has a video on taking out an Rv window and reinstalling. Hope this helps as I have just made you a pile of work. The old windows have this black rubber around them that squishes out and needs to be replaced with butyl tape(a better product than what was availableyears ago).

Put the trim ring on then caulk or wait a few days to caulk. Check out My 90 Classic restoration story. It is in the Off Topic heading.

Reviewed my restoration story. Forgot that I had used googone to clean up the fiberglass after the window was removed. Try it on the track before you apply the butyl tape. Don't you hate that when your memory fails you.!!

Thanks for your instructions, Sam. There are very helpful and we will tackle this in the spring!

We also have three more windows to reset in the spring. Lexell caulk can be purchased on line or at Ace Hardwear. It sells for eight $ a tube. Well worth it. Cheaper to do this than to totally rebuild due to water dammage.You can smooth out the caulk with your gloved finger dipped in undiluted dish soap. Other posts on file about caulk.