A simple spreadsheet with the right fields (contact info, last touchpoint, next follow up date, notes on their situation) can work just as well if you're actually using it consistently.

I'm going to be selling numerous houses over the next two years and am planning on using the same agent for all the houses. 

No clothes, nothing in the med cabinet, clearly nothing of value, and no payments...I'm securing my, OR my Client's property, and have done so on numerous occasions over the years, with zero repercussions.

Very desirable area close to numerous restaurants, shops and other businesses.

We are researching and considering our options to breaking into the field.

I know this is a very loaded question and a lot of people will probably respond “it’s different for everyone and your goals” but answer it for example if you had to restart in this field to be successful- my main question is should a beginner start in multi family and do house hacking or should they learn to whole sale or do syndicates?

If not there are numerous others to transact with.   

Whenever we sell a property, we move that property to the bottom of the spreadsheet to subtract it from our calculated fields for our portfolio - but helps to have it still around to be able to reference later on - like when it's tax time, etc.Part of the spreadsheet starts with Gross rents for the property, and then starts subtracting everything off of that from taxes, insurance, repair reserve, etc until I get down to a broad NOI of each property.  

You can take these to the field easily and setup.  

You need to know how and where to look for signs of leaks, questionable previous repairs that are hiding something worse, foundation issues, wood destroying insects, roof issues, age of plumbing and wiring (which relates to their remaining statistical life before needing full replacement), and numerous other issues.At some point, you will need to set up a bank account and credit card exclusively for the Rental income and expenses.