With that in mind, I’m considering purchasing four rental units over the next four years to build a stream of income that could help supplement my retirement by age 68.The challenge I’m facing is that the deals I’ve come across so far don’t make financial sense.

Something I caught within 10 minutes of looking at the financial.

Was truly one of the best financial decisions of my life. 

If those are relatively modern you have very little to worry about.

A lot of those people are financially vulnerable and lack resources to go against the seller.

Fractional TICs give owners the financial independence that has been associated with condos, without the need to wait for a condo conversion, a process which can take anywhere from 2 to 10 years depending on the specific requirements for the subject property.

It might cause me financial harm as I have to sell more stocks and might pay short term capital gains vs long term capital gains.

Learn what each one of these are, and see which makes the most sense to apply to your specific financial plan. $150 cash flow on any rental especially a triplex is dangerzone imo. 1 month of vacancy of 1 unit could destroy a years worth of financial gains.  

Their rates are good but boy, they looked at my financials and ask some funny questions such as asking for proof that I could withdraw funds from my SEP IRA account, and that I need to provide documentation to verify that  this employer sponsored retirement account allows for funds to be withdrawn, or if withdrawals could only be made in connection with the borrowers employment termination, retirement or death etc. everyday they sent me something new to answer.

Alternatively if they all love the deal, that's also likely a good sign.You can get a dog of a property in a crap neighborhood that will yield a 13.6% gross cap (not saying yours is), but that certainly doesn't tell the whole financial picture of how the asset will perform.