I know how to use Quickbooks but it has major cons (it's expensive, can't really easily build in features of a mortgage, recurring invoices are only for the $90/mo. plan), Quicken might be good but their property management is only on Windows, Stessa seems like it's pretty good but not comfortable with its terms (nothing in life is really free, folks!

If a certain recurring task isn't a strength for either of you, consider hiring it out.

So by not raising the rent, not only have you lost recurring cash flow, you also risk losing money when you sell what could be seen as a less profitable asset.I agree with Nathan G.

Consider local attractions, the weather/seasons and recurring events (e.g. festivals).

They are all pretty close to home in New England and are recurring annual vacations to the same exact spots, including the same Airbnb that a friend owns and gives us once a year for bargain rates.For our 6 week cross-country trip, we stayed in many Airbnbs. 5 star ones were hosted by people with a passion.

They also wont nickel and dime you since their goal should be to keep you as a recurring client.

I am not in anyway a part of the transaction, I am only trying to brainstorm some creative ideas to help him, and share some information as this is a once in a life-time opportunity that could help set him self up well, for a recurring cash-flow investment.   

One of the tenants has been a recurring problem tenant, causing significant damage to the apartment, causing me to receive complaints from the other tenant, and consistently paying rent weeks late.

See what costs are recurring and which ones are one time costs.

Bank of America also has its Home Grants Programs: "Our America’s Home Grant® program offers a lender credit of up to $7,500 that can be used towards non-recurring closing costs, like title insurance and recording fees, or to permanently buy down the interest rate," and "Our Down Payment Grant program offers a grant of up to 3% of the home purchase price, up to $10,000, to be used for a down payment in select markets.