. 🤔 Is base board heat typical in this area?

If this coach is in your market and knows the key players in the market, has used various property managers and can tell you the good ones, knows the loan brokers, knows the risks of investing on this side of town versus that, knows the tenant base for your area and what they are wanting from their apartments and what they can afford, than I would say a coach (maybe not the one you are interviewing) is worth it.  

Is there a difference based on age or is it based on the age of the roof and the windstorm mitigation done to the house. 

They'll be able to help and point you in the right direction to see if it's even possible to house hack based on your current position and market conditions.

It would give you the best of both worlds: You would pull out some cash to use on another deal and have a strong base of cash flow.

I'm based on NJ and my goal is to invest in MTR, single-family or duplex, near hospitals or universities. 

I think that is a decision based on your situation & goals.I'm not sure what your market rates, prices, or demand are, but I'd suggest analyzing both of the strategies you mentioned and see what numbers make the most sense.

Hopewell Handyman (hopewellhandyman.net) is an investor friendly and based in Alpharetta if you need help with repairs and tenant turns. 

Analyze different markets based on your goals.

Appreciation is just the cherry on top.The last few years Toledo somewhat caught up with appreciation but I believe we are capped now.It's a slow moving market and always behind the rest of the country.There is just not enough demand/infrastructure growth like in other markets to support continued appreciation.Historical data shows the Toledo market appreciating at the pace of inflation which is nothing to brag about hehe.IMO, it's a cashflow play and you should consider building a larger portfolio because it will be safer.Owning 1-2 properties can be a "hit and a miss" and really not the providers or PM's fault.There is a high likelihood of turnover so it's important to build a larger portfolio.If you experience "drama" on 1 or 2 properties, the other 4-5 are performing and can subsidize any losses incurred on the few that temporarily aren't performing.Wishing you much success