Hi John,
I am short sighted about -2.00 with .75 astigmatism. Over the past 40 years I have tried just about every combination of eyepieces, glasses and contact lenses known to man. I have found that the best option for me is to use high quality multifocals combined with long eye relief eyepieces which enable me to leave my glasses on all the time.
The advantages to me of doing this are many:-
1) I Don't need to change anything when I look up at the sky for naked eye views
2) I Don't need to change anything when I look through a TELRAD or finderscope
3) I Don't need to change anything when I read star charts, or the Argo Navis
4) I Don't need to change anything when I change eyepieces
5) I Don't need to change anything when I use my binoculars, both pairs of which also have long eye relief and can be used with glasses on.
6) I can actually see the people I am observing with and talking to on the observing field.
7) When I do outreach and share the views with others, which is very often, I advise all glasses wearers to leave their glasses on which greatly reduces the amount of refocusing required and makes it much easier for the subsequent observers to find focus.
8) When using large telescopes like 25"/F5 and 30"/F4.6 SDM's and Obsessions, which can have you 10 feet in the air on a ladder, I like to keep one hand on the ladder for stability and the other hand on the telescope / focuser. I don't need to find an extra arm to take my glasses off and still hang on when I get up the ladder.
A couple of important riders. You need to use decent quality eyepieces (within your budget) that have 20mm of eye relief (or very close to it) and most importantly that have a rubber eye guard which prevents you scratching a) The lenses of your glasses and b) the eye lens of the eyepiece. People will tell you they can use their X, Y, or Z focal length ETHOS which barely has 13mm of eye relief with their glasses on, but IMO this is just asking for trouble and something will end up scratched. Been there done that ($1,000 pair of Zeiss glasses lenses in the garbage bin). Some good options include Pentax XW's, Pentax XL's, several of the Vixen series including LVW's and LV's etc, TV DELOS, Nagler T4's, 31mm Nagler T5, 27mm, 35mm and 41mm TV Panoptics, Baader Hyperions and Orion Stratus etc. Their are quite a few others as well, including some cheaper Asian imports which are fine to use with glasses on. Some are fairly expensive some are fairly cheap. You usually get what you pay for.
I use multi focals but I don't use cheap ones. The more you pay for them the higher the refractive index of the plastic in the lenses, which, gives a much thinner lens, with much better optical properties than the cheaper thicker lenses. Most importantly the higher refractive index lenses are much thinner at the edges and give a much larger distortion free field of view. As your prescription strength increases high refractive index lenses becomes more important. They are also a lot lighter. Unfortunately the top quality lenses aren't cheap. A set of 1.67RI or higher multifocal lenses from a reputable maker like Hoya, Zeiss, Rodenstock etc. with all the AR and anti scratch coatings and the like will cost well west of $500, without frames.
http://www.allaboutvision.com/lenses/highindx.htm
The important thing to remember is that this is a very subjective thing and the above is what I have found works best for "ME" based on my observing situation and preferences. Depending on your observing situation and observing preferences there may be other options which suit your situation and preferences better.
Cheers,
John B