This appears to he more of a bite than you can chew.  

I'm all about the books that can be translated to have an impact in real life - not the kind that is just filled with new/cool ideas to chew on.

Fix and Flip and Wholesale strategies can work but be careful before entering those deep waters, its easy to bite off more than you can chew with both strategies, Id suggest you partner with a person with experience in either strategy before you make an attempt if you have no experience of your own.Good luck

Am I biting off more than I can chew?

You gave me a lot to chew on.

I know many times the offer may be rejected, and hope for a counter, and not a butt chewing.

Most real estate agents are brainwashed to try to sell the home for the highest possible price, even when that price is completely unrealistic.When this is the approach to selling a home that's in a state of disrepair, it makes it even worse.I can't count the number of times I've made an offer on the fixer upper and had them go with an owner-occupied offer instead (higher price) and then two weeks later when they back out the agent calls me up and tells me the other buyer bit off more than he could chew and now they want to sell it to me for the same price they were gonna pay... huh? 

Assuming I were to find a property that checks all boxes mentioned above, am I biting off way more than I can chew with this type of project? 

So bite what you can chew, rather smaller profit and for sure goes to your pocket, than a little higher profit and you have to think for a future claim, law suit, bank seizing properties or even IRS in the future knocking you down.

I was measured and honest in my description of my experience though and I do believe that they bit off more than they could chew.