When is buying high acceptable?

[Kate L.]

Hi everyone! I’m new to BP forums. I bought a multi/house-hack in the countryside in the Fall of 2020. I guess you could say we are just getting started with investing and loving it! Its in a small, quaint town, close to ski slopes and lakes. Prices here are ridiculous since Covid hit. Houses are selling in a matter of hours and there is no inventory. There may be an opportunity to buy the house next door but we would be buying high because the sellers want to take advantage of the hot market. For vacation rentals, we could get mortgage x 4 (at 100% occupancy, which I know is not realistic), and for long term, we could get mortgage x 1.5. It’s attractive to us because a) we could move into it and rent the second unit of our house-hack multi, b) we could rent it for short or long term and be living next door to manage it, c) we could have a place for family some day if needed d) we could have control over the look and occupancy of the neighboring property, which is important since we are right in town, e) we could connect it to ours via creative landscaping and create a compound of sorts. So my question is, is it ever worth buying high?