I entered a generic 'LASTNAME INVESTMENTS' (not knowing what to do..)  

But if you're middle aged with family / kids and want to use the cash flow to supplement lifestyle, take the less riskier investment of B/C SFR's.I for one is in a similar cross roads; currently weighing in the opportunity to buy a C-grade 106 unit vs. a 16-portfolio SFRs.

Now (recently) having sold that house, we're looking to reinvest the equity into flips (when the numbers/market allow for it) and rentals (preferably small multi's or small apartment complexes) - with the goal of building up a rental portfolio that supplements the W2 income (maybe one day near retirement it could replace it?).

It is a generic mailer.

I would treat the podcasts as a supplement to whichever formal education path you choose.

While it isn't something I do regularly for rentals [unless it is an incredibly high-end high-rent ($6K+/month), that is] I've found they are actually a great way to supplement the property's listing on sites like Zillow/Trulia/etc by providing buyers with an extra layer of depth. 

I ended up buying all out-of-state.In terms of your questions, I'll answer some generically more than specifically. 

Good tenants, all tenants, expect to pay market so as much as a landlord may think they are making points with tenants by supplementing their rents tenants have zero loyalty to any landlord. 

Unless you want a generic answer like set aside enough funds to allow you to operate during periods of extended vacancy. 

I am putting my career on hold as an Architect to grow a property management company here in CT, and plan to supplement my income with commissions from helping investors buy/sell properties.