If you see another RE market that you like better for investments for one reason or another AND you have the geographic flexibility to move there first AND it is somewhere you would actually want to live, then by all means, I'd advise moving their first to house hack ... having said that, I will also say that if you learn and know what you are doing, you can find great deals and make great money investing in RE in any market in the US, so of those criteria mentioned above, I'd more heavily weight living somewhere you would enjoy living.

I'm at the point where I want the debt reduction from the renters so the house will be free and clear in 8-10 years.

I really dislike truck driving but I purchased a truck in order for tax reductions.

House hacking combines the benefits of owning a great asset, an on-the-job lesson in property management, and a potential massive reduction in life's biggest living expense.

Income and debt are just opposite ends of a scale: put your money on the side with the greater weight (aka: rate).

She unfortunately had a death in the family yesterday so of course I don't want to bother her with this right now.I know I can go back to the seller and ask for a price reduction to meet market value. 

Plus you're saying that a $5000 budget increase = $10,000 price reduction.    

Your condo does have some measure of gap between these two sums, but its still tight and your HOA dues are a dead weight dragging down your cash flow.  

She suggested then to go in at $155,000 but still come back with a reduction after inspections, but I don't know if they will accept a post-inspection change in the offer price.Is it generally better with this company to go in at highest and best first, or do they accept low offers and counter?

I have used this old line in the past; do you think the mortgage company will give me a reduction in my payment?