Is your DSCR ratio greater than 1-meaning are you cash flowing (according to the lender's criteria of mortgage, property taxes and insurance (and HOA) if applicable).

My insurer is Erie, for everything including my umbrella. 

Insurance, bank accounts, credit cards, etc.You are probably making your life more complicated and expensive than it needs to be.

The double close or back to back closing is NOT illegal; it’s just darn hard to find a title insurer willing to do it.  

Technically, those sleeping over 12 built after 2016 are putting themselves in a legally liable situation if something happens as insurance companies may not cover them.

I plan on taking some introductory classes for plumbing + electrical + carpentry + ???

Then you will have a principal and interest payment of around $13,450.00 plus Taxes and insurance so add in another $2800 for $16,250.00 a month. 

I’m a Colorado commercial insurance broker and have a lot of carriers available in my agency.  

No mortgage payments have been  made by borrower since Oct 2015,  Bank is paying taxes and insurance at the sum of 15k a year, been in foreclosure for about 9 months, property is just under fair condition, owners are dodging the paper processors. 

That way you're not only reducing your daily balance on your principle, but you're also building equity in another investment at the same time.then, of course, there's the life insurance option...lol.You may be better refinancing, but then you have closing costs and you are forced to always make the higher payment.