However if this is purely investment (is no plans to move in after some time), you need to objectively do the math on your expected return given what you think price appreciation will be over the life of your ownership ( @Leo Kotschenreuther makes an excellent point) , weighting the risk of a downturn and your ability to continue to fund this investment, and compare that to using your 500k +2k/month to fund any other investment (Amazon stock, bonds, passive investment in a syndicated deal elsewhere.... ) We are holding our San Jose MF, but I've stopped looking for my next deal in silicon valley... property here is all priced for perfection (ultra low cap rates, neg cash flow, smells like 06-07!)

Actually a lot of the info you'd get from an operating statement (gross rent, expenses, NOI, etc.) is available on many listing websites like Redfin and realtor.com, albeit not as up to date as the MLS and not always accurate but that goes for all data provided by listings.Regarding MLS access: it is protected carefully with various methods such as keystroke tracking, IP address, simultaneous login etc. and agents can get in a lot of trouble for sharing their login info, which is good because within the massive database is a lot of private info that can be dangerous in the wrong hands like lockbox and security system codes.

I have a contractor who reached out to me and wants to partner with me. he wants me to secure the property and pay for the material and the work but wouldn’t that just be me hiring somebody?

If your after long term investments then there are other more secure ways of making a 7 to 10%+ on your money for example like buying A paper notes ( mortgage Notes) than a saving account or stock market.

How much do you ask for when asking for a security deposit?

Better for taxes, more secure and you have a bit more of control.

By paying it off you increase your security. 

I could move into a property that looks like a good deal (either in SF or the Easy Bay) and secure an FHA for 3.5% down by virtue of living in the property as my primary, rent out additional rooms, and essentially function as the property manager.

The one that is leaving wants his security deposit back.

Think of all the things that could go wrong and see if the lease addresses them: unauthorized pets or tenants, early termination, security deposit, lease violations, late rent, eviction, lawn maintenance, parking, etc.5.