Help deciding what type of tenant to go with

[Jacob Poppe]

I have a single story 4br/2ba house with a pretty large backyard that I rented out six years ago to four guys (all high school friends). Since then, they have all moved out and last year was the first year with four complete strangers in the house (whom moved in as others moved out). This year two of them are moving out, but two are pretty motivated to stay and have been looking for new housemates. I have also shown the house to two sets of candidates, one pair of couples with two dogs and one single mom (with a very good income) and her two sons. I should mention that I am hoping to build an ADU in my backyard in a year or so. Both my current tenants as well as the pair of couples have four cars. Street parking is limited so the guys do quite a bit of shuffling of cars as is. If I add an ADU in the back, having five or six cars would be a bit more complicated.. I could add parking by paving over the front yard to help with the parking situation, but that may hurt the curb appeal slightly.

So here are my options

1. Let the current tenants stay with two new tenants. This would be the least hassle for me as I would not need to paint or replace floors. Just touch up. One of the prospective new housemates wants a puppy and another has a cat. I have never had pets in the property.

2. Rent the house to the single mom with one son going to a local high school and the other in college. She owned a house in Cupertino (expensive area) and is trying to move closer to her son's private school. She wants me to install new floors, repaint, and also put in AC. These are things I want to do anyways eventually, but I am getting a sense that this tenant may be pretty demanding. I am concerned that after having eight different guys live in that house over the last six year, she may uncover a lot of little things I will have to fix constantly.. That said, she only has two cars..

3. Rent to the two couples. The guys seemed pretty handy, so may be able to handle a lot of the repairs. They only wanted new floors and paint, so I would not have to get the AC just yet.. They have four cars, which does not help with the ADU in the back next year.

I keep going back and forth between option 1 and 2 mainly. Anybody have experience renting a house that is in decent shape, but has been occupied by a stream of guys in their twenties to an older professional with high expectations? She already mentioned possibly remodeling the bathroom and her paying more in rent.. Over the last six years I might have had a half dozen things to repair, but generally speaking have been on autopilot. My main concern is having to deal with little things on a constant basis.. In some ways it would be nice to get the house up to a higher standard, but I am fairly busy with work and three kids of my own..

Thanks for the advice.