But, more importantly for future investing (and sanity) stay away from "guru's" and self proclaimed mentor's who have something to sell you.

As to the buddy I mentioned in Washington state it was the same scenario; he converted tax-free up to their standard deduction but above that he kept within the lowest tax bracket and paid the smallest amount of tax possible.Thank you @Basit Siddiqi for calling me out on this and giving me a chance to address my mistake; it's important people have the correct information.  

Of course making money is on that list, but more importantly, address the other goals which are just as important.

Agreed, I think these articles are primarily made as clickbait and designed to give homebuyers false hope of an impending housing crash.

That is the best case scenario, of course sometimes you get lied to and stalled, that's why it is important to always emply a double strategy and stay a step ahead.

It does not seem as important when you get started with one or two, but the issue keeps getting bigger

6 - Again, this doesn't predict anything, it's just a summary of what has taken place so far. 7 - This is important.8 - This doesn't matter. 

Unfortuantely, things happen that are out of your control.The insurance issue is such an important takeaway.

As for resources and connecting with other investors, take advantage of BiggerPockets through books, podcasts, articles, meetups and/or conferences! 

Depending on these answers one lender who charges 3 points could theoretically have lower total transactional costs than a lender who charges only 2 points and its important to understand all fees associated with each lenders origination process.