I am hoping you'll might know some rules of thumbs or guidelines for how much over asking price you are willing to pay?

IE  appreciation is gambling.. 

It technically can be achieved if you find a diamond in the rough, but the 2% rule is more of a guideline than a rule. 

Certainly don't give up... but maybe change your criteria and keep an eye out for something a little bit more safe for your first house-hack because having a stable foundation in a real estate portfolio is the real path to success in investment... risky purchases with big rewards might seem like a good way to start investing... but unless you have a lot of experience and cash in the bank, its just glorified gambling in my opinion.  

Then figure out how you are going to proactively protect your self (really good inspection, additional cash on hand, round up in repairs, get solid contractor quotes,strict tenant screens guidelines, treat tenants well so they want to stay, etc).

That was able to be conventional but they have a ton of products that they finance and hold so no need to meet fannie/freddie guidelines.

Sell: Tight lending guidelines right now.

Non-confirming loans do not conform to Fannie/Freddie guidelines for one reason or another.

Just like the 50% expense rule or the 1% RtV rule, they are guidelines to make investment decisions on. 

Keep in mind that many rural areas also follow strict city guidelines/ regulation.For example: Many rural areas are under development so you will need utilities.That being said many counties outside Houston call for specific area limits.1 acre only allowed for septic/water well.60 linear foot access road for emergency vehicles etc.That will totally impact your business model.