You need to do some deals on your own to show a track record before a lender will trust you.

You trained him and need to get your focus back on track .

Yes, you should be tracking mileage and expenses.  

If you run it all as one business, keep track of all of the finances together and report on them all together on your taxes then 1 account would make the most sense. 

I am a process guy so I like to set things up, give them some time, tweak them and track the results.

My view is there are some good investments and some marginal ones but they seemingly have a decent track record of paying off.

You are definitely on the right track with deals. 

Track everything you are responsible for and review that regularly and it might help you decrease expenses and increase the income.  

There are paid groups you can join that are run by someone who charges you but keeps things on track. 

@Charlie Ryan, I am a bit confused by your specified numbers, so I want to make sure I am tracking exactly what you are saying so please chime back in if I am missing something below.You have a property worth 430K.