A 1974 ranch that keeps coming back around on a live-in flip list

Here is a live-in flip scenario worth working through, because it is the shape most first timers land on. A 1974 ranch, 1,450 sq ft, three bed one and a half bath, listed at $289k and sitting 60 days. Original kitchen, one bathroom with a soft floor, roof at end of life judging by the curling shingles in the listing photos, with nobody having been up there. Nothing structural visible from outside, though an untrained eye will not see much from the curb. The buyer profile: $62k saved, W2 income that supports about a $2,100 payment comfortably, and a friend who does tile and would work weekends for cash. The rough plan: buy around $270k with 5% down, roof $14k, kitchen $22k, the bad bathroom $9k, paint and floors maybe $12k. Comps for renovated ranches on the same few streets run $370k to $395k. Live in it while the work happens and sell after two years so the gain qualifies for the primary residence exclusion. The open questions are the interesting part. Whether a 5% down loan even works on a house with a roof at end of life is the first one. The second is whether this is the right first deal at all against buying something boring and renting it, and almost nobody talks about what eight months in a house with one working bathroom actually does to a person. The decision on the table is whether an offer goes in this week or the search runs through the summer. Worth hearing how the room would weigh it.