Why does that sound fishy to me?

This would be pulling down horizontal siding on both sides of a garage of a duplex and replacing it with something else - vinyl, maybe?

This sounds like my dream job and something that would provide great experience. 

You could lose control of expenses very quickly if you don't know where each dollar is supposed to go from the beginning.The lump sum he provided sounds more like an estimate and not an actual bid.

Sounds like you have a good strategy to meet your goals.  

But, unless they've been clear they're going to fight it all, I'd focus on the fastest path to getting them gone rather than trying to get all rent due.You've got bigger fish to fry with what sounds like a rehab project starting soon.

On the surface - this sounds like a conflict - which is what I was trying to avoid in working with a "Buyer's Agent".  

This is like a forced savings where these funds will accumulate until you need to make a Capital Expenditure (roofing, replace hvac, road work, etc).Getting private money lenders at 4% for 6 years is very unrealistic.

And it sounds like you definitely need a new handyman - not wanting to work around mean people is no good explanation for late projects. 

Rehabbing a kitchen and bathroom and need to replace some of the old plumbing.