I have reached out to life insurance companies but they do not touch deals this small (at least the ones I spoke with do not) they like to be at $5-10,000,000 minimum. 

nope, these two actually have the documented ability to make the payments at a reasonable debt-to-income ratio.I'm coming up with ballpark $345k/mo PITI (my homeowner's insurance assumption might not be accurate, I didn't pull the actual property tax bill, and I don't know if there is an HOA so I left it at $0).

I don't think there's a scientific approach to learning this except for putting in a lot of efficient hours (like the 10,000 hour rule that Malcolm Gladwell discussed in his book), so it needs to be a combination of books, networking, speaking to local builders, Realtors, investors, attorneys, CPA's, insurance agents, and every other person needed in a real estate deal will get you where you need to go. 

Purchase Price: $374,900.00 Purchase Closing Costs: $0.00 Estimated Repair Costs: $0.00 Total Cost of Project: $374,900.00 After Repair Value $374,900.00Vacancy $420.00 (10%) Repairs $210.00 (5%) CapEx $210.00 (5%) Water & Sewer $300.00 (7%) Insurance $200.00 (5%) P&I $1,509.41 (36%) Property Taxes $347.25 (8%) Total $3,196.66 (76%)Monthly Income: $4,200.00Monthly Expenses: $3,196.66Monthly Cash Flow: $1,003.34Pro Forma Cap Rate:    8.04% NOI $30,153.00Total Cash Needed $93,725.00Cash on Cash ROI 12.85% Purchase Cap Rate  8.04%

Most 'standard' buyers aren't going to want to go through the hassle.

Can the cables be run underground, and  the transformer put in a standard ground box? 

Even if a conventional Fannie/freddie lender will not finance it, there are always portfolio lenders (who make their own decisions on a case-by-case basis), commercial loans (yes, they can be made on less than five units) and last but CERTAINLY not least, private individuals (a massively underutilized financing source, IMHO)I think your bigger issue might be insurance, rather than financing.  

But in no way it is going to be cheap by any standards.

Word of mouth definitely does travel so you'll find a good one as long as you ask people you know who just recently had work done to their house and if the pictures of there work looks good to your standard because bad work is unacceptable. 

Also, if you are licensed, you are held at a higher standard when it comes to selling property and other things and I don't want the extra liability.