Trailer access calculation?

I want to bring my trailer home to do some maintenance while we're all
grounded, but I'm not sure if I can access my house from the road. I
have a 90deg bend to get around and then the second issue is a short,
steep slope, which may ground the back of the trailer.

So my question is, if I measure things up, how can I calculate whether
access is theoretically possible? Is there any advice on the internet - I
can't find anything?

I don't want to just try the trailer for size because I fear getting it
stuck.