Once we owned some properties we could see how are assumptions panned out and repeat the cycle.There is opportunity, you just need to understand the constraints.

Title insurers are in the business of risk avoidance, not risk assumption so if there is a possibility of a later claim against the title, they will make a requirement to dispose of the issue prior to the issuance of a policy. 

My assumption based on comps is that we will be able to cashflow ~$800-1000 per month once both sides of this are rented and we move to our next project.

You start with an assumption that I do not hold: “assume my numbers are accurate”.  

My assumption is that this is non-warrantable, but you will be able to know for sure if you check the VA and FHA approved condos lists. 

You may be making assumptions here and since you lack experience, I would be careful about assuming too much.

@Edward Tamayo maybe not in your market but i know many others who bought 3 units or duplexes here with basement unit for owners to live in that live rent free and have 300 cash flow which is they put aside for repairs etc. you dont know every market to even state that. house hacking can allow you to live rent free or near it. no one said freeloading, your making too many blundering assumptions. crypto?

Gabriel - The expense assumptions "post refinance" look good to me with management fees, reserves/capital, utilities, etc...

If you went that route it sounds like you would need an "As Is" appraisal with assumptions because you want them to assume you're going to put $XXX 000 into the property and finish it with XYZ Countertops, and Y style flooring etc. etc.You could also ask a real estate agent in your local area to help. 

The big thing is you are moving over 100 miles away (assumption).