@Emmanuel Borromeo have you found that you get enough bookings through your website to make it worthwhile?

The additional equity after purchase is a nice bonus, and perhaps it'll be worthwhile to cash-out refi the property after at least 6 months to recoup some of your principal investment. 

While you want to minimize the financing costs, it also has to be worthwhile for your HML, so you might consider using $100k in hard money, then using your HELOC and/or cash (in whichever order you're more comfortable with) for the rest, keeping enough in reserve for the repairs and renovations. 

I don't plan to sell my current business, I've worked really hard and made many sacrifices to turn it into something worthwhile.

When I asked this, the PM is saying that if its just a matter of $300-$400 I should just forget it and its not worthwhile hiring an attorney unless damages exceed $1500.

Unless it is extremely cheap (which I'm sure its not), it would be more worthwhile to just have proper reserves.

If the area gets little better ( downtown area is slowly improving over las 6-7 years) , it would be a worthwhile investment. 

Worthwhile taking one to lunch?

Anything that is worthwhile takes time and effort.Yes it is worthwhile if you want to get rid of a cash flowing property and tie up your money for the time it takes to pay you back.I am owner financing a property that I got cheap to the existing occupants.

This strategy does take some work to implement, but it's been very worthwhile, so I would highly recommend doing it.