Hi Matthew! Finding a house under $750k is going to be really hard (I don't like to use the term "impossible" but near to it). Is this your budget?
Regarding option 1: Single family flips are really great in this area, entry is typically $1M+. I don't have a "deal finder" for you, but if you're motivated and qualified I can help you find an off-market by direct mail and cold calling.
Option 2: Be sure to check out any restrictions on short term rentals. With San Jose, I know if you're living in the home they'll allow you to air b&b/STR it for the whole year, but if you weren't living in it, you're only allowed to air b&b it for 6 months out of the year. There are some small single family homes in the Rosemary Gardens area of San Jose that are still selling for around $1M and are in a nice neighborhood and near the airport so they'd be great for air b&bing rooms. Not sure if that fits your budget or not but I feel like that area is a hidden gem. Otherwise townhomes/condos would be a good option since it's a lower price point and that market is softer than single family homes.
Option 3: Maybe the most cost effective option because of the purchase prices being sky-high.
There are currently 12 homes on the off-market section of the MLS that are <$800k and 2-3 bedrooms in Santa Clara county. Feel free to message me if you want the list or want to crunch numbers on a specific house.
