After spending quite a bit of time at the house in the last few weeks, I have learned of several maintenance issues that also have to be addressed (some replacement windows, some roof and gutter work, etc.).

In the end we had to renegotiate due to the roofs being in worse shape than expected so technically we were able to purchase the property for less than asking when it was all said and done.Originally posted by @Theo Hicks:Hi Hunter, Congrats on the deal!

I usually will hire out one larger piece of the work, like a roof or exterior paint a and do the rest myself.

It depends on where you live but enough for the down payment plus one of the most expensive repairs you can think of like a roof repair or minor foundation issues if you live in a place where this is common.

He and his brother have their own roofing business.

I have a flat-roof, single-family home in Camden, NJ that sprung a pretty substantial leak in the roof last night.

None of my refi appraisers have cared about a new furnace or windows or roof, as long as whats there is functional.   

Have them determine the useful life of the big ticket items like roof, furnace, ac, electrical and plumbing and use that to determine what you need in reserves and consequently what you can afford to offer on the house.You'll also want to look at the cash flow in case of additional vacancies keeping in mind what the vacancy rate is in your area.

I hired a chimney sweep company to clear a blocked gas furnace vent and replace a faulty vent cap on the roof at one of my single family rentals.

I own a roofing company and I am just getting into real esta