What to do with extra money?

[Matt Moldenhauer]

So my wife and I combined finances after getting married and are looking for ways to put our money to work. We each owned our houses before we got together. Right now we're able to set aside about $3,000/month. I struggle back and forth with the following options:

Payoff both vehicles in a little less than a year, which would give us an extra $850/month to invest. After that payoff our primary residence(about $90,000 owed right now) because it would not be taxed as income. After that, payoff the house she owned(about $69,000 owed). After that we would move to a nicer house and own two houses free and clear that are bringing in about $1,700/month. 

Payoff both vehicles, which would then gives us about $3,850/month. Do not payoff her house which we're currently renting and have about $200/month cash flow and purchase a new $80,000-$100,000 rental house every five or so months, etc.  

I look at it a couple of ways. Paying off the vehicles is like having an automatic $850/month coming in, minus the headaches and equity loss in a property. Owning one property that's bringing in $800/month cash flow is better than dealing with four that our bringing in $200/month. 

It seems like a lot of people are all about more more more when it comes to rental property rather than less free and clear property and higher cash flow returns? To me dealing with four properties that are generating $3,200/month seems MUCH better than 16 generating $3,200. I do realize though 16 generating $12,800 in 30 years though is better long term though. 

I'm I in the ball park here??