Well I'll tell you love11 that for most of my gardening career I did a single planting of maters on or about memorial day. It didn't matter if they were determinate or indeterminate but they stopped producing while the growing season should have still going strong.

(Not like I ever ran out though)
I friend who is really into his Maters plants a second crop around the first week or two of July and he picks and picks and picks...
As far as staking that just depends on how much effort you want to put into it. If you don't want to stake all 40 of you seedling just tell people you a practicing "French Intensive Gardening" and you will still get more Toms then you can use.
I have a gut feeling that you may be to late to be starting them in Jiffy Pots so let us know how your plan works.

Lowes must be pretty much be giving Tomato plants away right about now and I see lots of room to fill in your neat garden.
Most of all have fun.
