Purchase price: $272,000 Cash invested: $115,000 Sale price: $475,000 This was our first rehab project What made you interested in investing in this type of deal?

I began a quest for personal finance / accounting software that will help me keep tabs on my cash flow / net worth. 

BP has various tools to help you analyze your deals (rentals, flips, wholesale, etc). : https://www.biggerpockets.com/investment-calculators7.

I appreciate your insight on this as, like you said, this is a little bit of a complicated situation.

This will take some time as the credit bureaus are going to want to verify your business is legit. 

The property is in a B-class neighborhood, and while I’m comfortable managing coliving setups, I’m curious about any potential nuances around refinancing and insurance for this type of property.Are there specific loan types or lending policies I should know when refinancing a rent-by-the-room property?

When you move all of your insurance under one insurer, they can also bid down your individual policies to help save you money.

If this is how it works, do I ever go through the title company like I would in a normal wholesale transaction?

I think this principle applies to everything in life.

If you live below your means you should be able to save enough for this.