Outgoing server settings for MAC MAIL with multiple accounts?!

if i got paid to do this, my outgoing mail server issues would be somewhat amusing but as it stands they are really extremely annoying.
i have multiple email accounts (multiple addresses with multiple hosts - gmails, domain based email, me.com address etcetera).
does ANYONE know if there is an FAQ on what is recommended with respect to the settings on whether to tell mail to ONLY USE the one outgoing server and/or anything with the other settings?
i feel like i am in a pachinko parlor when i send mail because there is constantly an error of some kind and then i try dropping the mail through a different outgoing server by selecting a different one from the list and i just do this until it goes out. oftentimes i don't find out it didn't go out until the NEXT DAY becasue i am working and this alert gets hidden behind my other windows where i do actual productive work.
any ideas? i have two domain based websites (multiple emails with two SMTP addresses), two GMail accounts and me.com...
THANKS!

hi. CS. thanks.
do you know what this does as a practical matter? i mean, is it NECESSARY to check this box? will it try other outgoing servers and NOT WORK if you don't check this box? conversely, will it NOT try other outgouing servers if this one is unavailable if i check this (presumably the answer is yes here). i mean - am i likely to run into fewer problems by checking this box and i assume it is necessary to use the OUTGOING SERVER of the actual domain you are trying to send mail from as opposed to - for example - using GMAIL outgoing server for everything because you think you will get less errors than sending from your email domain outgoing server.
you know what i am saying? i mean, i get a bootload of errors and actually can't send mail these days even though Connection Doctor is telling me everything is hunky dory.
also, what is meant by "Offline"? do i have to go in and tell it to take everything on line for some reason and is this totally separate (telling it to go online) from checking things in Connection Doctor?
THANK YOU

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