Currently, I have a full time job in the fenestration business, and I was legitimately curious if the whole concept of "indoor/outdoor living" had a major effect on home values. 

To get this going here's my advice for getting started ASAP:Determine your buying criteriaThis is huge because you'll waste a ton of time analyzing properties if you don't know what you're looking for.

I keep reading mixed reviews..some say no waste of time and money - possible to grow as an investor without it and some say that it will help in the long run/perks of access to MLS etc etc.Would you recommend it?

Issue is a little different since you house hack...... its your house too, so living with slobs will directly effect you vs "sight unseen" and deal with the issue at turnover.You wont change them...not gonna happen.The cleaning service is a great compromise but fitting the entire bill yourself is not.......

@Theodor Morgan, buying a multi-family is a very common (and effective) strategy that many new homeowners/investors have employed.Run the property through the BP Calculators to find out how good a deal it is.

I've helped lots of budding investors leverage new technology to more effectively self manage their units!

If they don't work then don't waste your time, move on to the next one.

I do need more experience hiring good employees and managing effectively. 

Electric HVAC is outdated, expensive, and fairly wasteful.

Effective and proactive tax planning does and can bring US and Canadian tax treatment into parity.