As a couple of other posters have mentioned here, when purchasing investment property, listen to your gut. If you are already highly familiar with an area, possibly live in it and “know everybody” as Jazzman stated, then by all means, purchase an investment property you can walk to if you can at a fair price. A Pt Loma resident (unspecified tenure in Pt Loma but I happen to be aware that there have always been a few thousand Europeans in temporary and even permanent legal residence in Pt Loma) who wouldn’t likely be “familiar” with a condo w/homeowner dues in a much more congested area ~15 miles away. They would more likely be familiar with single-family housing in metro San Diego. (No, MM and SV/SM are NOT in “metro San Diego.” Even though they have City zip codes, they are considered “first-tier suburbs.”)
Chula Vista is actually closer to metro SD than SV/SM/MM and does not even require a fwy to get to SD.
I’m not saying Eve should shop there, only stating that nice investment SFRs are available in that area NOW. They are NOT inflated $100K+ from 2 yrs ago because most of them have been flipped or extensively rehabbed by their long-term owners. In other words, the price some of them may have to sold to a flipper in the recent past is moot, since they likely were a long-time rental wreck when purchased by the flipper. I’ve seen these flipping teams in action around here and, for the most part, they do a good job (and take the eyesore off the block thus lifting all boats).
Since Eve stated she had concerns (about repairs, and rightly so) on a circa 1925 home in NP, a flipped or rehabbed older home might just be her solution for an investment property. It is smarter to invest in something like this (that she, herself would be willing to live in) than pay $235+ in monthly HOA dues when she could take her chances that her tenants likely wouldn’t need $235+ worth of services from her every month.
It is customary in SD County for tenants of a SFR to pay all their own utilities including sewer, water and trash pickup (if applic) and perhaps on a PUD just gas/elec and trash pickup (if applic). $235 month is $2820 year, and in my book, that’s a lot of $$ thrown out the window when you can get the same or higher rent from investing in 1-4 units and don’t have to pay it. Tenants also tend to stay longer in SFRs (if the rent is reasonable) with Section 8 tenants staying the longest (abt 8 yrs, on avg, I believe). In this case, 50-80% of the rent is guaranteed every month to the LL. Applying to be a Section 8 LL is a bit of a detailed procedure but well worth it to a lot of owners of investment property. It’s just something to consider.
Contrary to popular belief, not all Section 8 tenants have kids and they aren’t allowed to conduct drug sales and other illegal activity in/outside of their units. If reported by neighbors and found to be doing so by the local HUD office, they will lose their voucher. The voucher is very valuable to them and it just isn’t worth it for them to give the appearance of anyone but a resident who blends in perfectly with their surroundings.