We have all experienced wiping out a year or more of positive cash flow in a single expense or numerous expenses in quick succession but realise over the long haul we will/should come out ahead if we buy right.

And, based on those perceptions, I would suggest you lean more to buying something essentially "ready to rent" rather needing serious work. 

I almost won a deal I wasn't even in the same ballpark as numerically, but my responsiveness and willingness kept me in the conversation long enough to get a sincere "thank you" which I don't underrate,I can't argue with saving money, I encourage it!

The perception is the deals are not there and that is true.....sort of.

Short-term vacation rentals is pretty much one of the main industries here with privately owned condos being more popular and numerous than hotels.

There are so many little things about this that are not complicated, but so numerous its mind boggling.  

The Milwaukee area has numerous REIA groups that you could frequent.  

(Talk to numerous lenders, actually.)

Yes I get the whole "dark art" perception that comes with the 1031 exchange. 

I have mailed numerous letters there with no response.