In the Cambridge-Somerville area, triple deckers in need of repair easily go for multi-millions, you need a lot of capital upfront for downpayment and rehab costs and you are relying on appreciation to build equity - the flip and condo conversion is a popular option in these areas. 

You start your investing with multi or whatever but separately.

Finance of America has a 90 seasoning advertisement. 

So, Decide which kind of investor you want to be (SFR, Commercial, Land, Tax Liens, Passive, HML, Multi-Family, Notes, Fix & Flip, Buy & Hold, "Subject To", apartments, duplexes, assisted living, REOs, Foreclosures, Short Sales), etc.

But, I was hanging out with people that were both single family and multi family investors.  

If the updates are done as advertised, I wouldn't use such high numbers for CapEx and/or R&M.  

Case in point we inherited 4 tenants in a multi.

If so, yes, you can deduct a lot of expenses, but they have to be advertised and available by then on Airbnb.You cannot "deduct" renovation cost, you can depreciate them.

My wife and I own our primary residence, and hopefully by next summer will be ready to purchase a multi family.

I have been searching for multi-family houses in my general area for a while and it is tough to find multi-family houses to house hack in decent neighborhoods.