Obviously you tell this person that “only trusts you” to sell and pay the taxes and pocket $50k minimum more than selling to you.

The people paying you $10,000 per month to rent your property are doing so because they need or want the use of the property, not because you’re a “people” person.4.

Could I be stunting my growth as a person by not changing my environment and forcing myself to adapt? 

CA might be different and where you generally need accreditation is when you are using other people's money and promising returns.  

We talked for several minutes, then out of the blue he said he would offer seller finance if he found the right person to sell to.

If it actually goes through, my plan is to use this money to fund my Roth IRA after I recover my basis.How much do attorneys typically charge and who pays?

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I hear a lot about standard personal loans, mortgages, etc - but do banks or smaller players consider situations like the above?

Do you feel that putting the money in will force you to stay the course? 

Get Hard money loan to pay off debts while I get HELOC either on Free and Clear2a. or the primary 3.