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To quote Anthony Wesley, "this hobby is not for the impatient".
There are some things you can do to alleviate the issue of cloud. Remotely operating your equipment in an area with better cloud prospects is the primary way of dealing with the problem. You don't need top of the range gear either. There is a chap here in SA doing remote work with an EQ6, GSO scope and has just spent some money on a mono camera. He has done a lot of problem solving but now getting results in a dark sky area.
In terms of my own expenditure which is well over 100K, I have the cost per use in remotely operated equipment, down to $3-$4 per use. It took nearly 10 years to get the cost down per use, but the secret is to operate the scope every clear night available. Using it autonomously allows the system to be accessed by phone. So while I am out socialising with my wife, the system is paying back the investment.
So my advice is persist with cloud, make other plans on how to use your equipment and then implement them.
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