Any guidance is appreciated and I know it's not tax nor financial advice, just your thoughts.

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.

Too bad you can't buy something owner-occupied, put 5% down with the best interest rate, live in it for 12 months (and fix it up), rent it out and repeat the cycle.Here's some other info you might find useful:----------------------------------------------------------------------------------------------------------------Recommend you first figure out the property Class you want to invest in, THEN figure out the corresponding location to invest in.Property Class will typically dictate the Class of tenant you get, which greatly IMPACTS rental income stability and property maintenance/damage by tenants.If you apply Class A assumptions to a Class B or C purchase, your expectations won’t be met and it may be a financial disaster.If you buy/renovate a property in Class D area to Class A standards, what quality of tenant will you get?

Prioritize your financial stability.

Don't limit your future financial freedom to just where you live today.

If two funds need money for litigation support, that seems telling on the current financial condition.

I believes that well-planned real estate investments can open the door to financial freedom and generational wealth.Welcome!

I even try to unsell them on the business by sharing my financial losses, litigation,  market shifts, permit purgatory, shady contractors,  clouded title issues,  paranormal activity, squatters, mold, etc.

At one point I talked to my financially advisor and he said that it would be smart for me to open a HELOC on the property, but not draw from it, except in the case of emergencies.  

For the lease, can you list the girlfriend as an occupant rather than a co-tenant since she won’t be a financially responsible party?