Flipping is a great way to make a lump sum in abort amount of time.... But things can go wrong, hidden issues emerge, some renovations can drag on too long. The ability to make a lot is the real goal here, if you want to make quicker money that doesn't last, this is the way to go. These tend to be riskier, but can pay off a lot when it all goes well.
Buy and hold is the best option for longer term goals, and the way to truly build wealth. Placing good tenants is key, that makes this whole renting process so much easier, be stringent on screening. Make sure the HVAC, water heater, and appliances work well, those are the most common issues that I deal with maintenance wise, that can be a big financial hit when renting if you're not ready for with a reserve. If you do it right and find a good deal to rent on you can cash flow, and I would always recommend aiming to get cash flow on a rental, breaking even is ok, but you should always cash flow some amount from a rental. If you do it this way you get a nice monthly income, build equity as you pay down the loan, and in most areas your house will continue to appreciate value. Even if you only rent it for a 5 years or so you can enjoy all three benefits mentioned above (equity depends on your loan and how much principal is actually getting paid). Also I would recommend leveraging, don't buy properties outright to rent. I recommend learning how to do a cash on cash analysis and you will see the benefit to leveraging.
Really depends on the goals with your investing, but buy and hold is always going to be the best option, it is a continual income stream, you do not have to hussle all of time, and you can cash out down the line if you want once the property has appreciated nicely. Sounds like you have a good bit of experience, and good knowledge to help your Dad understand benefits to both sides. Best of luck to you both!
