Hi and welcome DJ
Grab and go is one of those grey areas, what's grab and go for one may be a real pain for someone else. What you can comfortably lift and how far you need to lift it to are the big factors.
A while back I bought a good quality 80mm refractor and a heavy duty photo tripod for this purpose, but in the end it desn't get used when I have larger scopes to play with. I have a C9.25 on an EQ5 on a portable pier mount and a Tak Mewlon 180 on a Meade LXD75. Both equatorial mounts. I regard both as grab and go for my purposes. I simply open the french doors and carry them out into the backyard, plonk it down with the RA pointing roughly south and off I go, it really is that simple. The Mewlon and LXD75 I can comfortably carry the 10-15m I need to go in one piece. The C9.25 I just carry the OTA out seprarately, but can manage the pier mount with weights etc as one (not suggesting this last is good for the back though).
A lot of people are put off by equatorials and think they are hard to use. You only need to fuss with polar aligning if you want to do long exposure imaging (don't need it for planetanry web-camming) or to use go to (have it, don't use it). I've spent many hundreds of happy hours of visual and planetary imaging with both my scopes and I've bother with polar aligning.
Your suggested choice of a 5inch skywatcher maksutov would be smaller than my scopes and you really should be able to carry them around in one piece. One thing to remember though about Maksutovs is they take an awful long time to cool-down (1-2hours) and this more than anything makes them less than ideal as grab n go scopes (I overcome this a little for my SCT by using a cat-cooler). A smaller refractor would be better, but as Phil mentions you might be dissappointed with the views after a 10 inch dob.
Maybe a trolly, a dozen roses and a five star meal, might be your best and cheapest option
cheers,