As much as possible I'd recommend getting really clear on your goals in life and how real estate fits into those, and then iterate from there.If you are buying at a distance (specifically you're not moving from house to house and collecting houses as you go) then it would be a great simplifying factor to buyer AN asset or two with many doors, but there are other ways you could structure it so that small multis are the way to go.So, back to the root . . . what do you want to accomplish in life, and what role does real estate investing play in that?

Does he have accounts in collections?

For me all rents, fees collected, and other property-related income goes into the Income account and from there is distributed to:Operating ExpensesTax and InsuranceLoan PaymentsOwner PayThis has worked well for me since I instituted it around 3 units in.You could break the distributions into any number of categories that you'd want, but the "secret sauce" to the system is to literally move the money so that it lives in the relevant account and then spend from there.

If this property is in an area where you need a bulletproof vest and a machine gun to collect your rent, I would not buy it.

I do not get any money from TurboTenant, nor am I an owner or investor in the company.They have a referral program where they will send me a $25 home depot gift card for a referral - you don't have to use the referral codeStessaStessa is a website that I use to track all my expenses.It is another free site and you can pull reportsYou even can upload receipts.Roofstock recently purchased StessaCompletely freeZillow Rental ManagerI use this to collect rent.Free for the landlordTenant only pays a fee if they use a credit card to pay rent.

We settle on our 3rd residential property in a few weeks and feel it's time to start collecting rent online or through an app.

For all those landlords who are having trouble collecting rent you will want to look into the rent relief program for your state. 

As a syndication it might work but youd need to collect about $5m from investors willing to take this risk, not easy in general, especially without a track record.

I would agree that general networking and education help lead you to a market,  but it gets overwhelming in where you turn to collect data from there. 

If I understand correctly, Airbnb automatically collects Anchorage muni 12% tax from the guest (see article here) and I don't need to worry about it.