Now I'm struggling to pull the final trigger on my 2nd property which is a residential property in WI.

I agree with @Loren Clive, the only way to get a deal at the auctions is to go to all the auctions, have the cash sitting around, and be ready to pull the trigger when one of the properties goes for the right price (except when it's a good enough deal to justify paying 5% more at confirmation).

@Jacob Dodge I've been looking in Mobile, but haven't pulled the trigger yet. 

If the #s work and it is an upcoming area, do your research and pull the trigger.

I think the best thing you can do before you pull the trigger is to answer a couple of questions, and that will make everything more clear to yourself on if you should do a deal or not.

Reading: Lastly, I read either a hardcover book or a kindle (old school with no backlight or sidelights on lowest setting) (no phones, tablets, laptop screens) until I am dosing off and basically about to drop the thing on my face (this has happened before :D) then go to sleep :)It's definitely a set of habits, but once you get yourself conditioned to fall asleep after these triggers it gets easier.

Just make sure and get your accountants blessing so you do it in such as way it doesn't trigger a recognition of gain.

Also, could someone suggest realistic project milestones that should be used as triggers?

I'm proud of you for pulling the trigger!

There is a major basement water issue and we currently have a quote from a local guy but before I pull the trigger I would like to get a second quote.