How do you assess and manage risk when financing a large-scale fix-and-flip project?

I have a rental in a large lot - easily enough to subdivide to 2 parcels, plus the house sits at the edge of the lot.

If you have a large amount of properties, probably best to have a contractor do it for you.

But, to retire off of real estate, one either needs a lot of time to pass, or needs a large base of capital.

Not only for the reasons you mention (easily manipulated, depending on format), but also have next to nothing to do with what your operations will look like.While I do agree that you should try to verify income, both through lease review, P&L, and if they will share: bank statements and tax filings, at the end of the day, I don't put a ton of value in seller financials, for many reasons.  

He wants to focus on large ticket items for property managers: roofs, turns, hvac replacement, whole house painting, things like that.

So, if MTR are really LTR, then we have a large inconsistency with marketing channels.Secondly, “normal” LTR residential property leases run 12,24 or 36 months.  

There are only 14 rentals in our rather large area of the lake.

It really depends on you and how involved you're willing to be, especially if any of your current at-large operators don't work out.

This one is in a small town outside of a very large city.