Even if it is an accident, still counts :) My personal journey is similar to yours - I just keep house hacking once a year and keeping the previous one as a rental.

They should be able to tell you how much of the potential rental income with count towards the income requirement and your CPA can guide you on how much you can comfortably afford in a housing payment. 

Reading the description reminded me a bit of writing an essay back in school where I was trying to pad the word count and put in a bunch of superfluous words and sentences. 

Record keeping is essential since profit is what you paid plus what you put in (every receipt counts) subtracted from the sales price . . . . so the better your records are the more you can offset the sales price and the less you pay in taxes but without records, you have no leg to stand on

Also the details of the bed count and sq ft were incorrectSeems to be all scams, but I have never done this before, and hoping someone on here knows how to navigate Craigslist more successfully than I do!

I really hope you are checking the other sold comps, ideally 90 days or less back, comps from 9 months ago don’t count, even 6 months ago be careful 

In your case you offered what made sense and would not cross that line. 

You can always cross collateralize the property paid in full with the purchase loan. 

I wouldn't necessarily count on a 30% rent increase.

If you have no, or negative CF, that means you lost money because you have no way of recovering your cost...and equity doesn't count in cost recovery.