We had to convert years ago to Rent Manager as our property management software for this very reason.

I gave them a brand new SimpliSafe security system to install in a vacant house.I also paid them 1/2 of the rehab estimate to get the work done.

ROI is too low and to high risk income security wise.

.#4 Compile Your Prices into a Spreadsheet or Estimating SoftwareOnce you start to get a better understanding of Labor and Material costs you will want to store this data into a spreadsheet or software that you can use to help you streamline the estimating process.The Book on Estimating Rehab Costs comes with a spreadsheet that you can use to help you populate your own database of labor pricing and material pricing.

Does anyone know of a good software program to track my expenses?

You are also allowed to discriminate against people who are rude, messy, or can't come up with first/last/security at lease signing.  

A better way in my opinion is a promissory note secured by the property and title transferred to you.

What is the simplest software for managing 15 to 20 units properties mostly 2 family to 4 family dwelling?

And don't even get me started on their lending to people with the "security" of a W-2 vs business owners that know how to make money.

I have experience with a similar association for my rental property in WA.https://masslandlords.net/laws/security-deposits/