Instant cash to purchase other investment properties or someone paying off your condo for you with a bit on the top every month?

Overall, also bear in mind that the fundamental purpose of property insurance is to bring the dwelling back to the state it was in prior to the loss, or to "make you whole." 

While Fixing and Flipping is minor fixing and instant profits.

Finally, there's a strong ethos for living in SFH in my area and a negative connotation with apartment dwelling. 

v=qHpc80xVNFk Dave Meyer in podcast rents out "accessory dwellings" which sounds much easier then legit duplex conversion.

I hate to be a debby downer, but if it's on market and isn't gobbled up within a week or two there is probably a reason why... most good cash flow deals sell instantly and are off market deals purchased by cash buyers. 

So, if I were to sell it by 2020 (within 3 years of turning it into rental), I pocket the entire capital gains on the property (roughly $65k) but I will instantly lose my $750/monthly cash flow from rent as well as depreciation I each year.

It's currently off market and I can put it under contract in an instant.

He instantly replied with "Well let me know when you do I've been looking to diversify my investments and I'd love to invest in RE with you.

My job doesn't have the best work/life balance and it's something we're hoping to change using the power of real estate.My wonderful partner and I want to focus primarily on multi-family dwelling rentals using a buy and hold strategy.