I would, personally, let him exhaust all his funds on the purchase and then you come up with a loan that finishes off the acquisition financing and then holds the rehab funds in escrow in an account you and your brother sign off on for withdraws.I do not think I'd put a lean on the property. 

handling the whole transaction start to finish ? 

The outcome is going to be one of the largest homes in the neighborhood with stunning finishes and fingers crossed with parking!

We would like to convert the basement (which is already finished) into a 5th unit, it just needs a shower and a kitchen but that is a project we would get into while living there. 

If it sucks, pay someone to finish and fix your work.

These machines would likely cost millions of dollars, and it is unlikely they could handle the more intricate tasks of finishing the houses… think carpet, showers, stoves, air conditioners, garage doors and their openers, screened porches, and the list goes on.Just my 2 cents All the best!

I’d buy it today because for me the finish line isn’t a year from now, the finish line is 7 years from now, 10 years from now.And once the market heats up, buyers come out of the woodwork and you might miss that good property is hopes of being the one to snag it at a perfectly timed market bottom.Just my approach…..

Better finishes?

Start to finish it takes 2-4 months in Virginia.

After renting out the finished basement and one of the main units, we'd be paying a very comfortable amount for our part of the mortgage, and upon moveout we'd be breaking even with PITI + maintenance, capex, vacancy which is what we wanted to achieve.