Taking a security deposit is easily accomplished with a property management software, which are honestly super cost effective and easy to use once learned. 

Personally I'm using Google Drive, but it's getting pretty slow to run as I keep adding properties and photos - and it's not great for narrowing down/creating a map of different locations.Does anyone have any tools/software they recommend for keeping track and comparing deals?

99% of software like that will require credit card on file, i think its like only 100 per month. if you dont want to pay just cancel prior to trial ending!

I've decided on Buildium for my software. 

If you rent by the room, I would recommend using rentler as a PM and advertising software.

If I could go back to 18 I would get my degree in something that I liked but mainly helped me make as much money as possible (like software development) then I would take that money and be laser-focused on investing in real estate.

I think the only way to deal with this sometimes is to use a PM for a tenant placement service only, then have the tenant pay rent to the me landlord directly through online PM software and have your handymen, plumber etc that you dispatch when there are repairs needed or routing maintenance (like HVAC servicing).

I would set myself up as a contractor setting up the software for the landlords but would that still constitute collecting rent? 

We also invested heavily in software to manage our business - when I say heavy - I mean $25k+.

These properties are new purchases in the past few years and what the city has on file is what the prior owner submitted.We would like to get in front of this requirement by providing the floor plans of each property with the rental permit application.Is there a web site, software, or company, etc. that BP members know to gather this floor plan data by location?