Very first questions to ask when buying a site? First considerations?

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...It is easier to present the points as considerations, about which we ask questions, then draw classifiable conclusions.

In crude terms, these are the ways that QA defines problems:
A critical fault is one which is about to cause a system to fail without immediate attention.
A major fault is something that will become a critical fault if it is left unattended for a matter of weeks.
A minor fault is a problem that can be seen, but does not materially affect the function of the system.
If there is no problem, the matter under consideration is satisfactory.

Starting at the top. First consideration - "Is the asking price in the budget range?"
That is a yes/no which has to be satisfactory before doing more work - if it is not, the site has a critical or major fault.
If you can see ways of finding funding to purchase the site, the problem may diminish to minor - eg, you might be able to finance the purchase but be forced to use the revenue to pay off a loan for a few months.
Concluding question - "might it be worth doing more work investigating this site?"

Second consideration - "The niche".
Does the site niche fit in with your other sites? Will it compliment your other sites? Will you need to set up a "bridging site" to supply links from your own network?
If you need to pay for links, you have to add that into your cost estimations.
Concluding question - "Is the site niche satisfactory, or acceptable (ie it has minor problems)?"

Third consideration - the "site type".
Are you familiar with operating a site of this type? Are you confident that you could learn to do it quickly?
If you have to pay someone to do it for you, that has to go into your cost estimations.
Concluding question - "Is the site type satisfactory, or acceptable (ie it has minor problems)?"

That's your starter set of thoughts. One thing you learn in QA is that every auditor has his own company assessment sheets for auditing, and there is usually something you can learn from someone else's sheets.
There's a heap more questions to ask - obvious parameters to consider are the ratio of buyers to traffic, and if you might be able to see ways improve the revenue rapidly. You need to know where the traffic is coming from - if all the links in are indirect, going to domains which are 301'ed to the site, that could get switched off so easily.

You can add more questions to the list, following my concepts - or you can improve those concepts. This is only a guideline example, I'm always open to constructive criticism.

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