So he's cash flowing well on it, he's acknowledged that my situation will be different so I might need to raise rent.3) I think these are all valid questions, but the owner raised these himself too.

@Jim Bice this actually sounds pretty reasonable to me given the situation you described.

I applaud Brian for personally reaching out to respond to the situation and make sure things are addressed going forward. 

I find that automation often adds more complexity and time to a given situation rather than helping you save time.

Hi Charles, I'm also based in Honolulu with young kids and in a similar situation to you, have also thought about buying an investment property in Japan that we could use part-time and rent out at other times.

Year 0: ($2,000 - $1,700) x (1 + 2%)^0 / (1 + 5%)^0 ≈ $300 in today’s buying power.Year 5: ($2,000 - $1,700) x (1 + 2%)^5 / (1 + 5%)^5 ≈ $260 in today’s buying power.Year 10: ($2,000 - $1,700) x (1 + 2%)^10 / (1 + 5%)^10 ≈ $225 in today’s buying power.Year 15: ($2,000 - $1,700) x (1 + 2%)^15 / (1 + 5%)^15 ≈ $194 in today’s buying power.So, if you purchase property in a city where rent increases at a slower pace than inflation, the amount of goods and services you can buy will decrease over time due to inflation.Here is what I recommend:Purchase in a city that possesses the following characteristics.Significant and sustained population growth.Rapid and sustained appreciationBalance negative cash flow, interest rate buydown, and increased down payment to create an acceptable cash flow situation today.Refinance when rates fall to increase cash flow.

If not try a keyless entry situation that allows you add a temp code that will expire after the work is completed.

A few quick notes before I go into more detail on how I approach situations like this:- As mentioned in other replies, a 401(k) match should (almost) always be taken advantage of.

.🤝 A Place for BothHere's the thing - it's not really an either/or situation.

For me, weekly check-ins and just being real with my team—like saying, “Hey, I’m not sure, let me check on that”—have saved so many situations.