Sure, you are playing it cautious. But I see a risk of analysis paralysis setting in: trying to tie up all the loose ends while the difficulty rises and the window of opportunity starts to close...
Anyway I think a collaborative venture is a great thing to do. But it's going to have to be nimble to be successful.
Actually, while you may consider that the 'window' is starting to close, that is only based on the current value of Bitcoin in relation to the expenses to establish hardware dedicated to mining Bitcoin.
If you consider that regardless of the expenses for mining Bitcoins, that there will still be Bitcoin miners since there are ~140 years remaining to establish all the Bitcoins.
I think a better comparison is for individuals to depict the costs of mining using their own hardware and electricity compared to costs for investing in Bitcoind Pooled Mining Association. In this case, for users that want to contribute towards mining Bitcoins, they would still have an opportunity to do using either of the two methods suggested above depending on which is lesser expensive for them.
I believe it is still useful to establish a mining association that offers best performance at best value regardless of how difficult it is to generate a block or the cost to operate*.
* Unless the cost to operate is comparably more expensive than users establishing their own individual hardware setups to mine.