From the tenant side, both cost the same to use (free for ACH, under 3% for credit/debit card).

Set up auto debit from his account directly to yours so “remembering” isn’t an issue.

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Pretend it's a debit card and pay that balance down every month. 

I prepaid a year's worth of insurance which the company failed to account for and couldn't give me an explanation for months why I was being double charged for insurance purposes.

I'd say you can invest 50k & take on 5k a month in debit.

Hey all,Does anyone have any experience wrapping closing costs and prepaids into their loan?

There are ways to subsidize it, such as getting a seller credit, or taking a slightly higher interest rate in exchange for a lender credit to pay that and/or other costs and prepaids. 

After accounting for APR costs, non-apr costs, points, UFMIP, and prepaids our total cash to close is $19,828!

I do have a checking account associated with the 401k as well as a debit card, so it's quite easy to manage expenses that way.