I know absolutely nothing about the commercial lending space, and am already googling my way through that one, but I'm in a not so unique position of not knowing what I don't know so...

Suffice to say, the analogy is doing a paint job on a unique car - but leaving the mechanicals in place without addressing reliability. 

I am currently looking at purchasing a SFH with the intention of turning it into a top/bottom duplex and here's why:1. I have already talked to the city and they are fully on board and are excited to see more housing ...

I own and live in a 3 bedroom, 2 bathroom ranch in a desirable area suburb of Charlotte.It's my primary residence and only property.

If you're doing an STR, are you in a desirable travel destination?  

(We could frame those ideas in positive language as desire for safety vs desire for a goal.)  

Purchase price: $529,000 Cash invested: $30,000We moved to Eagle River, Alaska and found a home with an attached MIL so we could afford to get into a desirable area.

Hey @Eddie Ibrahim this is a unique question that probably requires more than quick answers.

There are many multi-millionaires who built their fortunes via single fam houses.One of the best things about this approach is that it allows you to get the home with an owner occupant mortgage (which has the best terms).A few considerations:Single family properties often appreciate better than multifam properties (especially if they're in highly desirable areas).If you decide to sell it, a single fam will often be easier to sell than a multifamPeople rent single fam homes all the time, if the home is in the right area (you'll need to do your own market analyses to figure out where people are renting single fam homes, and what they're paying in rent).If someone can afford to rent a single fam home, that does not necessarily mean they could afford to buy a comparable home. 

It boasts a unique set of historical buildings, beautiful beaches, and many wonderful restaurants.