Since I'm investing in such old buildings I pretty much bake in new HVAC, new roof, new electric, + basic cosmetic upgrades anytime I'm kinda pre analyzing a deal because 99% will need it sooner than later in South City. 

I use a basic task manager app (like Todoist or Notion) and set up recurring tasks for each unit.

If so, my opinion is that you are being penny wise - but pound foolish.A more basic questions is WHY - why are you forming this “partnership”.  

For investing principles and deal analysis, The Book on Rental Property Investing by Brandon Turner is excellent, it covers cash flow, evaluating deals, and basic financing strategies.

BiggerPockets is one of the best platforms for learning the basics and surrounding yourself with people who have already walked the path.

Two quick moves: set a simple buy box so you’re not chasing everything, and analyze a handful of real listings each week using a basic cash flow calculator, then sanity‑check rents with a local PM.What’s the first deal you’re aiming for—property type, price range, and target rent—and which market are you eyeing for that first purchase?

Don't forget the basics, buy property for less than what it's worth, not just because you are getting just a little money down.In negotiations, break everything down into pieces.

That’s normal in appreciating/coastal markets.Paying off the mortgage is basically buying a bond at 4.375%.When you pay off $265K at 4.375%, you’re getting a guaranteed return equal to the interest you’re no longer paying, plus the cashflow jump you mentioned.

I recommend listening to the top STR podcasts as they will cover all of the basics for you.

Basically 100% interest or 12% per year.