It depends how what you want, if you will put in the work and if you will still have money left over to invest.

Meaning thats likely 30+ minutes without much traffic, more on a busy day. thats not really close, people are going to choose closer properties first and you will get the leftovers. and as others have mentioned, its not a house that screams "Im near Disney" it is decorated like a house you could find anywhere. 

Cook plenty and don't be so picky with your leftovers where you are free to microwave them for a quick on the go bite on the way to wherever you are going to get out of the house. 

I’d prefer owning outright a handful of properties that can cashflow $1500-$2000/month (which is even lower than your $2,500/month).It’s whatever you & your fiancé think is best though if I were in your position, I’d be just fine with selling & buying 3 properties around $250,000 purchase price ($750,000 total) with a few hundred thousand left over.

You will also need reserves left over after down payment and closing costs as well keep in mind.and this is likely the only structure you would find to help you with the your down payment anyway.

Had some left over and told the guy to use it for the next job. 

That's only $400 left over for everything else.

If it blows through theirs and there is left over liabiilty to need to hit you, then... it some huge claim... 

Then I take that $75k left over and buy a $300k property with it the provides me cash flow and in five years may be worth $330k and the car would still be worth $15k.Thats why.

Then, potentially either straight up sell if the profit is there, or move into one of those units, take the leftover money, and keep doing this.Obviously, the numbers would have to make sense, and that's what I'd have to learn.