There are varying opinions on this but mine is: cheap never goes out of style.

Maybe his investing style is just way more passive? 

This platform on Bigger Pockets is a great source of information where you can ask questions and also learn from other investor questions.

I'm an out of state investor looking to understand and learn the Pittsburgh market.

New to real estate I hope I can learn about the market on here.

This approach would allow me to learn with each deal and minimize initial risks.2️⃣ Go Straight to Multifamily: Instead of starting with SFHs, I could spend time learning the multifamily business and go directly for a 20+ unit building, maximizing scalability from the start.I have no experience with either strategy.If you were in my position, which strategy would you choose and why?

I still own this property and in only 4 years the value increased about $100k with cashflow of $1000/mo Lessons learned?

A lot depends on an individuals motivation, dedication, learning capacity, decision making capacity, analytical ability, time available, support system, mental state, and yes, luck. 

That's the other challenge that i've learned, with only one month as SD, if the tenant leaves even in a relatively new build the fees add up. 

that we’ve learned in our 24 years, managing almost 700 doors across the Metro Detroit area, including almost 100 S8 leases:Class A Properties:Cashflow vs Appreciation: Typically, 3-5 years for positive cashflow, but you get highest relative rent & value appreciation.Vacancy Est: Historically 10%, 5% the more recent norm.Tenant Pool: Majority will have FICO scores of 680+ (roughly 5% probability of default), zero evictions in last 7 years.Class B Properties:Cashflow vs Appreciation: Typically, decent amount of relative rent & value appreciation.Vacancy Est: Historically 10%, 5% should be applied only if proper research done to support.Tenant Pool: Majority will have FICO scores of 620-680 (around 10% probability of default), some blemishes, but should have no evictions in last 5 yearsClass C Properties:Cashflow vs Appreciation: Typically, high cashflow and at the lower end of relative rent & value appreciation.