Whenever you pool investors money together, you need to consider securities issues.Maybe you're thinking about the limits that Fannie and Freddie put on borrowers that want to get investment loans on residential property?

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?

Otherwise, it must be  officially done by the City. 

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?

My biggest concern is just the fact that we might not officially go under contract on the house we like best until a few days after we close on the first one in a few weeks, with our FHA loan, and we definitely won't have 20% to put down on either. :-/  Definitely appreciate your advice and will see what we can find out about investor friendly loans with our broker.

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.