All the what-ifs, and hidden costs that might break me.I'm narrowing in on a live-in/ house-hack in a duplex with an existing two car garage, with the intention to immediately convert that into an ADU for myself, until I soon thereafter refi. and start the process over.Maybe on the next one I can have the confidence to go with hard/ private money cash buy/ rehab. 

I'm looking for some opinions and insight on what a person in my position ought to do. I have a strong W2 income but few investments that will benefit our family when retirement happens; let's call that 10-15 years do...

Banks make you fit their narrow criteria while loan brokers shop your borrower profile with dozens of banks to find the one that works best for you.

I think you should first narrow down your criteria i.e. price point and area.

Currently driving for dollars throughout the whole area and would like to narrow it down a little bit and avoid the not so great areas.Thanks for taking the time reading my post and looking forward to networking and growing with everyone.

In a world of options, how can we narrow it down to the quality ones that aren’t raping pockets, and protect the future?

To Brian's point Worcester changes by the street so focus in on what you're looking for in the investment property and then try to narrow down your search. 

If you haven't already I'd suggest finding an investor friendly realtor down in that area and start analyzing as many deals as possible to narrow down your market. 

In any case, I'm working on narrowing down the other criteria, but honestly I was mostly focus on making sure the numbers work before getting too picky on all the other stuff class, etc...  

That said, I think your first step should be to narrow down your focus.