If you have to think twice about the monthly holding cost, that is a red flag.Unless you're getting the home at a discount, I would look elsewhere for your first investment, preferably something that you are at-least breaking even on.

Depending on municipality, that addition could cost you thousands in the further when the city finds out. 2) I’d only spend 45k down if I were getting over 8k back in my pocket on year 1. 3) It doesn’t even sounds like you’re getting a “deal” at all with your friend discounting you 5k.

I'm looking at purchasing a property that doesn't have a bathroom on the ground floor.

The home has 10 bedrooms and 11 bathrooms, as well as a pair of bedrooms and bathrooms perched above the four-car garage.

Its has new floors, kitchen, bathrooms, etc....

You may not even need a discount off the current price, even if it's at FMV.You can't re-sell it for higher than it's being offered at while it's listed for sale. 

Extra bathrooms and bedrooms not permitted.

I paid $60,000 cash for the off market deal, which was probably 25% discounted.

That said, I asked for 30K not only for sprucing up the duplexes but also as a discount for the charring that I will have to factor in when I go to sell the place.

I moved in and immediately replaced all of the carpet flooring in the house with engineered hardwood; I re-painted the entire interior; I replaced all kitchen appliances with new ones that I found at a discount at an outlet/scratch and dent; and replaced the water heater.