I have almost 100k saved and am more than willing to spend whatever I need to. 

Even if I have to wait 6 months and spend $50K on a different buildout, I'm still doing better by month 15. - I believe that companies and the economy as a whole have begun a long-term shift towards back to in-office.

In addition, once you get the experience of managing from afar you can manage from anywhere and invest anywhere.

How does one take the owner finance situation to a bank and turn it into a 30 year loan to hold without an additional down payment of 20 percent ?

Would it  be possible to get an additional roommate where you and your boyfriend live?

Not adding any additional living space, just dividing the two units, putting a kitchen in one of them, and probably not having to add a bathroom to either unit.  

If they say put up higher railings, additional smoke detectors, etc, complete it promptly and document it.I've been in the landlord business for 20 years, and I've always kept my properties to code and well maintained. 

I’d greatly appreciate your thoughts or suggestions on alternative approaches we might consider. the pro and Cons of this approach recommended by a lawyer, when it comes to tax, refinance, etc..Additionally, if you know of any CPAs or lawyers in your network who specialize in real estate investments and asset protection, I’d be grateful for a recommendation (DM me)Looking forward to your insights, and thank you in advance for your help!

Quote from @Gabe Chase: Quote from @John Underwood: Just curious how much do you spend annually on all the 3rd party software you use? 

If your property does not have additional upgrades that make it worth more on the market then you likely need to drop the price.