@Tim HoltFrom my experience, house hacking can work well if you focus on minimizing living expenses and setting yourself up for future cash flow.

Challenges like this can ultimately set the stage for a better-performing asset in the long run.

Luckily I was in a buyer's market at the time, but about 75% of agents did not even respond to me and I could not set up appointments online because I was not a MLS member.   

Of course, nobody wants to be the test case, but I've never heard of IRS treating money from a loan as income, ever.I think you would be better off with a long closing date on the purchase and sell your exchange property fast so you can do a conventional 1031, receive conventional financing with one set of start up fees/costs, etc.

Her contract says nothing about set up fees or early termination; I gave a generous offer to keep $400 as a design fee, but she sent me (2) $30 deadbolts and said the Technology Fee was non-refundable.There's other, better STR management companies out there.

., more than half of the calendar year) for the Borrower’s personal use and enjoyment"This means that you can only book it out on STR platforms for half of the year (50% max occupancy), which really sets a cap on your max income. 

Having intentionality in your actions and goals set to enable you to reach that 1 real estate transaction milestone is important and will ultimately help you reach that sooner. 

I have investors that I set up loans with private money that only use this method because of the speed.

House hacking can also be a solid way to offset expenses early on.It sounds like you're diving in with a great mindset and skill set—being handy and managing yourself puts you ahead of the game. 

Pro:- it’s trained to look for safety risks, expensive repairs- within minutes analyzes entire disclosure packet of hundreds of pages- works as another set of eyes that looks for things you should be watching out for, likewise of a companion - great to quickly learn of property conditions from the actual documents while on the go (given that you still follow your own due diligence process)- beta is freeCons:- still in beta- can’t share report directly unless copy and paste- only core documents (home inspection, pest, roof, tds, hazard, solar) are supported but not regional specific disclosures like hoa- estimates it provides aren’t accurate- not mobile friendly