I got in touch with two contractors yesterday and they each wanted $500 to walk the property and give an estimate.

I think you'd do better by getting in touch with guys in the business, seeing which of their properties perform well, figuring out why, and trying to find something similar will be best route. 

Sometimes you can touch up one wall and paint another wall in the same room.

Each to their own mate,Personally, I would never touch new construction.But there many ways to skin a cat, right?

Hey @Alba Cheung, I am guessing you have a cleaning team in place, if so, there are low cost, high touch options or high-cost, low touch options.

I'll definitely add you to my team list, we just made an offer on a Kihei condo and will keep in touch for sure! 

You touched on my exact struggle in this instance.  

I wish you well on your investing adventure and encourage you to get in touch if you need help or have any more questions!

You might want to touch on ownership in that agreement as well, that will be important.

I'm paying about the same to live in my house as I was splitting a 1-bedroom apartment with a roommate, but now I'm seeing that appreciation, sweat equity, and tax benefits you touched on.I love reading comments and posts like yours to give me a refresher on why I got into a house hack in the first place.