Before I go to deep in answering these types of questions I always like to ask these two things.1.

Do people suddenly have deep pockets out of nowhere?

The factors here are several layers deep...1- The threshold decision is rooted in local ordinance and zoning...if you're in an area with tight local ordinances you're fighting with the people that live in the neighborhood before you ever reach the city zoning folks...this can go one of many ways2- ROI on the conversion...you're first stop should be with a local architect...they are worth their weight in gold when navigating a project like this and will wade through the regulatory waters much better than you...and a simple phone call may be telling to whether the conversion would be permissible.The extension of this is the cost of the renovation in relationship to the rents received...the stars would really have to align to say you should spend a significant amount of cash to convert a performing building with 4 revenue streams to serve another function (but there is more to this)...and the cost of construction (and lumber in particular) is 5 fold what it was 1.5 years ago...3- As you indicated...exit...I think the only rational reason to convert a 4-unit would be to get condo status or single family/ shared wall and sell one or both of the units to an end buyer (you are basically paying the role of a speculative developer here)...this is happening frequently in locations like Olde Towne East and Merion Village...hard to demonstrate how successful this has been, but it seems far fetched reasonable consumers would pay the same for a  free-standing SFR they would for half of a "duplex" or condo, but who knows for sure.Either way you look at it you're in a residential appraisal situation on the comparable sales approach....4 unit buildings are still "single family" homes. 

I have such a deep love for the Rogue Valley and love calling it home. 

Your best bet is to speak with a commercial/portfolio lender who is willing to help you get creative or find someone with deep pockets who is willing to go in with you on this property. 

Or is this because I haven’t looked deep enough into the market?

Excited to deep dive this one.

Our advisor has done very well for us regardless, but it's time for us to take a deep dive into the finances and compare some real numbers between stocks and RE.We currently rent in NYC and that exact question is the crux of my other question in the forums, https://www.biggerpockets.com/...

It is like nothing I've ever experienced in my life.The point of this post, however, is not to lament my woes or even go on a deep dive about how much Covid sucked (because it was pretty awful).

Start with podcast epoisde one on the bigger pockets website and listen to as much as you can from the beginning, the ones from back then with Josh and Brandon, I feel and just my opinion and could be wrong were much better because a lot of the guest were actually doing deals not as much people coming on the show as a syndicator looking for investors Josh also ask a lot of how to questions and get deep into how they were doing deals and you can learn more.