It's a lot of work, but would probably be more fruitful than blasting out résumés on Jobbing or Monster.

Where did I put my laundry basket?

IMHO the best way to view the two is one is a basket of golden eggs and the other is the goose that lays the golden eggs.

There is an old adage in real estate about putting all your eggs in one basket.

Start out with the older neighborhoods in town...That's always the lowest hanging fruit. 

I was panicking thinking I wouldn’t live long enough to enjoy the fruits.    

Everyone knows a lot of the low hanging fruit is not so easy to find anymore, but I see on Redfin that people have closed deals that never showed up on the MLS. 

The low hanging fruit deals with light rehab and low margins are for the weak ;) Did you work with any real estate professionals (agents, lenders, etc.) that you'd recommend to others?

On the other hand I feel that I need every spare cent to pay bills and save up for our next property to make it further in life and it feels like I might be paying towards something that never ever happens, I'm torn.With the retirement annuity, I do believe in not putting all my eggs in one basket and it’s a very good idea, but I feel that if I take life cover and a retirement annuity my expenses will equal my income, and I'll just be living from pay cheque to pay cheque which will put a huge setback on buying our next property.FYI, I'm 31 years old if that makes a difference?

IMO, the frugal would likely much prefer to grow their own fruits and vegetables, shop for raw quality ingredients, and invest a bit more time and money in their food in the short term to cook their own meals with quality ingredients in order to achieve the long term benefits of eating more healthy, while still saving money over going out to eat.