Hi Horeb,
I was asking the same questions myself when i first started diving into the real estate industry last year. Here's some information that i hope will help you out:
1. Brain storm a high level business plan of what you wish to do in real estate. Do you want to retire early? How much net cash flow are you trying to receive from each property? What do you think will be enough for you to live comfortably? 70k annually? How many homes do you have to buy to get to that point? Having this basic guideline will help (at least for me it does) you identify if the particular property in question falls in line with your game plan.
2. Narrow down up to three cities/regions where you would like to invest in and stick to those three areas. The reason i say this is because it is VERY easy to switch from one city to another on your realtor or zillow app which will make you feel like you're just treading water with no real momentum occurring.
3. Do a thorough research of the real estate agents. You want someone who is honest, efficient and knowledgable of the industry. You also want someone who understands the type of real estate you're trying to buy. The real estate agent should know that you're not looking for granite countertops or vaulted ceilings etc and that you want low maintenance. Yelp/zillow/realtor.com all have ratings for the real estate agents so you can scroll through there and see what their previous customers have said. In this industry reputation is very important.
4. Do a thorough research of the property management companies in the cities you are interested in. The reason i say this is because you will be trusting this company with your investment so you need to make sure that they meet your standards. Call them and ask them what their vetting process is for perspective renters? How much are the fees to manage your property etc. Also ask if you can speak to a referred customer. This will help you figure out how they do business and what to expect if you decide to go with them. It doesn't even hurt to go out to the perspective city and meet the property management team. It will give you some peace of mind seeing the city and what kind of properties that are out there.
5. ASK TONS OF QUESTIONS! Go to meetups! if you don't have any around you create one! There are tons of knowledgeable people who are passionate about this industry and can speak for hours about it.
6. Use the bigger pockets tools to analyze properties. I use the rental property calculator and its awesome. That being said you will see that 90% percent of the properties you analyze will not meet your requirements. Don't let this scare you. You'll find that one property that ticks off most of the and it'll be so sweet once you close on it and you get that monthly check.
I feel like I'm forgetting some things but hopefully this gets you moving in the right direction! I am also in San Jose so let me know if you'd like to meet up some time to discuss!
Thank you,
Nizar Basma