I had a similar mindset and started...in the sense I bought house hacks in areas whereI wanted to live and worried a little less about the dollars and sense and just made sure it worked for me!

That makes more sense overall.A lot of us here only buy in vacation areas.

I am very new to this idea, so it's possible that one of these options just doesn't make sense.

My opinion only 2 cases make sense for the seller 1) they have few options and this presents the best means to get out if a bad situation.  

Does that make sense?

And YES, far FAR too often I am seeing people stack up UN-realized expenses at a compounding rate, to give selves a false sense of "profit" on whatever monthly/quarterly capital there moving around. 

Very few people operate their LLC correctly and therfore this just gives them a flase sense of security.Moving into a LLC can also trigger the due on sale clause.

Be conservative because demand can go up or down at any time as can the laws -- a good general rule of thumb for STR is to make sure it still makes sense as an LTR.

There are exceptions where bankruptcy can make sense, but this isn't one of them, in my view, based on what you've shared.

However, if you're a W2 high income earner or business owner, I can't imagine it makes any sense to flip houses, mail mass post cards, wholesale, or build lead gen websites with the value of your time being better spent other places (such as learning about real estate and increasing your income through proven means), such as at your 9-5pm or growing your business, and your real estate is a long term process and you don't need "home run" deals to qualify or make it work.