Wear and tear I don't care... but holes in the wall = the drywall and my time to fix it.

While we do have cash saved up, we'd prefer to work on our credit for another year before looking at getting a mortgage or commercial loan to possibly do a fix and flip.If you were us, would you a) use our cash to purchase, fix and flip something older and cheaper outright which seems like a huge undertaking for our first deal, b) use our cash as the downpayment/skin-in for a hard money loan (balloon) while we work on conventional qualifications to refi at a lower rate in 12 months, c) My in-laws are in the process of purchasing a seller-financed home and are interested in "renting-to-own" their place to us.

I only care about my own analysis. 

c. Are

What I am saying is when you go and buy groceries, do you care what the grocery store paid for it's merchandise?

I have seen many cases where it never worked out and the people had to take the huge loss and move on with no recourse.You just have to be extremely careful.

Be careful what you put in writing,a lawyer can use it against you in a court of law.The tenant is within his legal rights to demand a receipt for rent paid and the reason is not up for debate by anyone.You must furnish a receipt within a certain time period established by your local state law.You can furnish it electronically,US Post Office mail,or in person.Also,that statement regarding possibly moving into the apartment might been seen by a judge as illegal harassment of a paying tenant.You seriously should seek legal advice from a competent attorney and let them write responses to your tenants with the correct legal language.

If you are not careful the seller will feel like it is a scam.Good luck

It's not in too bad shape, but was a smoker's house and hasn't had any cleaning done in years.Based on a quick walk-through I'm looking at internal painting, minimal external painting, carpet replaced (or removed to get to the hardwood floors where possible), a bunch of minor repairs to things like gutters/eaves/etc.In a perfect world, this relationship would continue to care for the property as issues occur in the future.

I think it's more about adhering to contract law and being careful to not violate agency laws.