Your house-hacking goal is achievable with an FHA loan, even without related field experience, as long as your income supports the mortgage. 

An attorney and escrow achieve the same result for far less.A lender will only lend on what an appraiser appraises.

The only question is what kind of balance is best.

Subject-To is an extremely high-risk play for anyone not capable and/or comfortable with selling, refinancing, or repaying 100% of all Subject-To debt balances, all at once (if they have multiple). 

You may have to invest more time up front to cultivate the right relationships but these are the relationships that will help you grow and borrow funds that outpace your balance sheet.

We've seen tremendous interest from investors seeking larger balance investment property HELOC's or home equity lines of credit. 

Given your strong financial position, the best way to move forward is to balance growth and risk management.

It's not going to come easy, but if you have the right group of people with experience and net worth, it's very achievable.

Think New York, San Diego, Los Angeles, etc.The problem with that though is a) You may not be able to afford anything there, or b) If you can afford a downpayment you'll be eating negative cash flow.In short, the highest appreciating markets may cost you too much per month to participate in because they have large negative cash flow.So you need to find a market that balances the two.