They could all use quite a bit of rehab work and are currently being rented for 25%-35% below market rental rates due to the condition they are in. 1) Single Family - 2bd/1baGross Cash Flow = $3,000/moCurrent Market Value: $1.1M2) Single Family - 2bd/1baGross Cash Flow = $2,700/moCurrent Market Value: $1.1M3) Single Family - 4bd/2 full bath + 2 half bathGross Cash Flow = $0 (Vacant, house need a LOT of work)Current Market Value: $1.84) Duplex - (2) 2bd/1baGross Cash Flow = $4,500/moCurrent Market Value: $1.8M5) Commercial - 6unitsGross Cash Flow = $11,100/moCurrent Market Value: $2.5MTotal Gross Cash Flow Across 5 Properties: $21,300/monthApproximate Net Cash Flow (after PITI) = ~$14,000/month (property tax assessment is EXTREMELY low because it was inherited, total tax assessment for all 5 properties is <$2k/month)Market:Location: San Mateo, CaliforniaNeighborhood: Grade B+In a perfect world I would like to double or even triple this net cash flow so that myself along with my sisters family can retire early. 

We owned it 10 years, did very little to it by design & the assessment had tripled by the time we sold it, for way less than the assessed value.I see in some of the southern states tax assessments are doubling & a friend in TX tells me his tax assessment has risen 200% over the last few years. 

Triple net or modified gross?  

Also, you probably have double or triple glazed windows now - how energy efficient will bulletproof glass be? 

I didn't accuse anyone with abuse or user damages.I have tried to be transparent about the issue, explaining I have been threaten with fines for doing work, service call fees are double/triple the costs, and it just comes down to, its cheaper to buy a new dryer ($475)To add to the issue, I have a 3rd year law student and the other unit is some 24 year old that works at a Big 4 Firm who think/view this is an unimaginable inconvenience, and the law student is citing all sorts of legal codes on why blah blah blah is a certain way, but obvious has never been to small claims courts where paperwork and circumstances matter greatly, or the costs of having to deal with the this stuff is problematic.

It almost tripled in value after 5 years....I then 1031'd that property (thank you @Dave Foster !)

He came back and today noticed more water damage on downstairs room ceiling ( almost triple size of visible orignal water spots damage in downstairs ceiling), after checking bathroom upstairs he noticed it was dripping from hose of one of machines running in bathroom.

It's quite possible that if you offer this "tough, rude tenant next door" some money to allow the roach treatment, all your problems go away -- mean neighbor, roaches, the whole brouhaha.As for the tenant being tough and rude and on Sec. 8 -- if you're going to be operating in any property class short of triple A lux, you're not always going to be dealing with tenants who have significant people skills.

But I bought one in 2012 that has tripled in price.

As kind-of expected, Proper quote is double of CBiz and triple of Foremost quote.