Buying house from my current landlord?

[K.C. Marsh]

Hey, everybody. I'm an inspiring investor from Louisville, Ky and I'd like to get some feedback on making my first deal. For the last couple of years I've been renting a 3 bedroom house with 2 others and it's time to break the cycle. Although it's been a while since the owner has mentioned it, he said that he may be willing to sell in the future. If this is a possibility, it would certainly be the most convenient way to start out, especially since I have a lot of stuff. My current roommates have been great for as long as I've known them and I know they are financially stable. Hard to find better tenants in my opinion.

Living there for the time that I have, I know that it doesn't need any major repairs and he's even updated several areas as well. House hacking would free up what I currently spend on rent and what doesn't go to repairs, would go toward another investment opportunity. As much as I'd love to get it for 70-80% of the market value, he may not be willing to let it go for that...although he may.

That being said, what would you all do in my position? How close to market value would be worth it since I'm mainly interested in cash flow? I know you should make your money going in, but assuming I can't, would it be worth my time? I know without numbers it's rather difficult to say, but I'm just looking for ideas. I'm trying to do a bit of homework before I sit down with them. I'd hate to look back at this deal at a later date and realize I only did it for convenience reasons. It seems a great option now and although I could be making more elsewhere, I'd still be living rent free in a house that I'm already settled into.

I appreciate everyone's time and I'm glad to be part of this group. Hopefully, I join the status of investor in the near future. Cheers.