Hold the retail indefinitely for yourself??

But I worked out the numbers and showed him that within 5-7 years we would have enough passive income to keep us going indefinitely. 

If there is a second outbreak or the SIP is extended indefinitely, there will likely be a grand exodus from the city. 

Since a lot can happen in 2 years, lets just play on worse case scenario, in that your future life situation requires you to use your side of the garage space for longer than 2 years (indefinitely).

The guy i want to kick out pays 625 on a 1 bed that is running 875-1K in my market.The good thing is that i factored all this in and can afford to pay for the building indefinitely if i have no tenants (great w2 job) so i have leeway if they leave and can take the time to get a quality tenant (even though its not ideal for cashflow if they do because i want to buy more property).

Ultimately, we'd like to retire at a reasonable age, travel, have a legacy that teaches our kids about hard work AND money as well as continue to invest indefinitely. 

There might be a max of a one-year requirement on there (maybe) but it's not indefinite, I know that for sure.

Cons are what I just mentioned about having to live there indefinitely, and also that I would be getting it at market price (unlike the distressed single family deal I found off market) unless I find an off market multifamily deal.

I worked in banking from 2006-07 and quit when they announced indefinite promotion freezes thanks to the economy.

Then you have to buy something of equal or greater value.You could do the 1031, buy the new property/s and then still do a cash out refi if you wanted to.The 1031 will allow you to postpone capital gains taxes, maybe indefinitely if you keep doing this or hold the property you buy and pass it on to your heirs.